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Best road trip ideas from Boston

Calling all road trippers! If you’re searching for an exciting destination to look forward to on your next journey from Boston, look no further than these alluring Northeast cities. 

Best Road Trip Ideas From Boston

There’s nothing like the great American road trip. Trading wings for wheels gives you the freedom to explore off-the-beaten-path destinations at your own pace, and helps keep vacation costs down. And the best part? When you’re ready to escape the hustle and bustle of downtown Boston, you’ll find much of the Northeast is right at your fingertips!

Consider booking a vacation home on FlipKey and save even more during your getaway. Whether you choose a secluded cabin, cozy beach cottage, or an urban apartment, rentals provide extra space to stretch your legs and all of the comforts of home, including a full kitchen, free laundry, and wireless Internet.

From the breezy beaches of the Jersey Shore to classic New England vacation spots like Portland, we’ve mapped out 13 great road trips from Boston. So hop in the car, hit the road, and explore the ribbons of highway that wind through the region.

Plymouth, Massachusetts (40 mi, <1hr)

Drive down to Plymouth from Boston.

Revel in American history and discover where the Pilgrims first landed almost 400 years ago: Plymouth. Visitors from near and far flock to this gorgeous seaside destination to see landmarks like Plymouth Rock and the Mayflower II, a replica of the ship the Pilgrims sailed. Had your fill of history? Drink a Cape Codder cocktail while admiring Cape Cod Bay from the back deck of your rental or lounge on the sprawling, sandy beaches.

Our Top Restaurant Pick: CabbyShack

Our Top Activity Pick: Jenney House Museum

See all Plymouth vacation rentals on FlipKey!

Rockport, Massachusetts (45 mi, <1hr)

Rockport is located approximately 25 miles northeast of Boston at the tip of the Cape Ann peninsula.

If you’re searching for a road trip from Boston that won’t leave you cramped in the car for hours, Rockport is an ideal choice. Located on the rocky jut of land known as Cape Ann, this coastal town boasts award-winning dining and attractions, without the congestion of a big city. Sit in the sand as the waves wash over the shore, or hike along Halibut Point. Rockport is the picture of tranquility!

Our Top Restaurant Pick: My Place by the Sea

Our Top Activity Pick: Rockport Music

See all Rockport vacation rentals on FlipKey!

Hampton, New Hampshire (50 mi, 1 hr)

Book a rental in Hampton, NH.

Within an hour’s drive of Boston, Hampton is an easily accessible destination just over the Massachusetts-New Hampshire border. Here, succulent seafood, eclectic shops, and picturesque beaches abound, and you’ll never run out of things to do! Take a dip in the ocean at Hampton’s eponymous beach, watch sand sculptors in action, or fly a kite high above the dunes—the area is bursting with possibilities.

Our Top Restaurant Pick: The Goat

Our Top Activity Pick: Cinnamon Rainbows Surf Co.

See all Hampton vacation rentals on FlipKey!

Providence, Rhode Island (50 mi, 1 hr)

Find your rental in Providence, RI.

A blend of historic sites, modern attractions, and big city conveniences make Providence worth a stop on your next road trip from Boston. Fill your days in the “Renaissance City” feeding giraffes at the Roger Williams Park Zoo, exploring the ins and outs of Brown University’s campus, or sipping an espresso in the historic Federal Hill neighborhood, also known as Little Italy. At sunset, hop aboard an authentic Venetian gondola for a romantic cruise down the Providence River.

Our Top Restaurant Pick: GraciesProv

Our Top Activity Pick: RISD Museum

See all Providence vacation rentals on FlipKey!

Ogunquit, Maine (75 mi, 1.5 hrs)

Drive up to Ogunquit, Maine from Boston, Massachusetts.

For easy access to beautiful Maine beaches and a bustling town center, follow New England’s spectacular coastline up to Ogunquit. Sandwiched between the Atlantic Ocean and the Ogunquit River, there are endless opportunities for outdoor recreation. Set sail from Perkins Cove, climb Mount Agamenticus, or wander along Marginal Way, a scenic cliff walk that spans more than a mile. With fresh seafood, sheltered beaches, unique art galleries, and vacation homes for every budget, Ogunquit is the idyllic road trip destination from Boston.

Our Top Restaurant Pick: Northern Union

Our Top Activity Pick: Ogunquit Museum of American Art

See all Ogunquit vacation rentals on FlipKey!

Kennebunkport, Maine (90 mi, <2 hrs)

Coastline in Kennebunkport, Maine

This quintessential New England destination, nestled along the coast of southern Maine just 90 miles north of Boston, is best known for its fine white sand beaches, quaint historic districts, and remarkable art galleries. Enjoy the sea with a whale watch or charter a boat for a unique perspective of the local lighthouses. Prefer dry land? Bike, walk, or drive down scenic Ocean Avenue for jaw-dropping views and a glimpse of former President George Bush’s summer home.

Our Top Restaurant Pick: Bandaloop

Our Top Activity Pick: Seashore Trolley Museum

See all Kennebunkport vacation rentals on FlipKey!

Old Orchard Beach, Maine (100 mi, <2 hrs)

Visit the beach in Maine.

Just 30 minutes up the road from Kennebunkport, Old Orchard Beach sits along a 7-mile stretch of golden sand. Bask in the sun at the city’s namesake, Old Orchard Beach, or plan a day of family-friendly fun at Palace Playland, the only beachfront amusement park in New England. In the afternoon, cool off with an ice cream cone at the pier, or kick back on your rental’s balcony overlooking the water.

Our Top Restaurant PickJoseph’s by the Sea

Our Top Activity PickPalace Playland Amusement Park

See all Old Orchard Beach vacation rentals on FlipKey!

Saco, Maine (100 mi, <2 hrs)

Views in Saco, ME.

Take your pick of outdoor activities in this small town on the southern coast of Maine. There’s the Eastern Trail that winds through the woods of Maine, zip-lining adventures at Monkey Trunks, and fishing charters on the Atlantic. If you’ve got kids in tow, head to Funtown Splashtown to cool off without the hassle of loading the car with beach gear. Consider a vacation home near Saco Bay with a BBQ grill, beach views, and plenty of space to make your trip extra special!

Our Top Restaurant Pick: The Run of the Mill Public House and Brewery

Our Top Activity Pick: Funtown Splashtown

See all Saco vacation rentals on FlipKey!

Portland, Maine (110 mi, 2 hrs)

Find a rental in Portland, Maine

Known for its luscious lobster rolls, picturesque shoreline, and historic charm, Portland is a haven for vacationers in New England. At just two hours from Boston, it’s a convenient destination to get to, too. Stroll along the brick sidewalks, sip on a pint at a local brewery, or play skipper for a day exploring the open waters by boat. Spend a long weekend in Portland and you’ll leave Vacationland—Maine’s official slogan—feeling positively refreshed.

Our Top Restaurant Pick: Duckfat

Our Top Activity Pick: Children’s Museum & Theatre of Maine

See all Portland vacation rentals on FlipKey!

Provincetown, Massachusetts (115 mi, 2.5 hrs)

Rent Provincetown vacation rentals

Gorgeous beaches, charming lighthouses, unique art galleries, and an exuberant town center—there’s only one Provincetown. Situated at the very tip of Cape Cod just two and a half hours from Boston, this scenic spot is a popular road trip destination for those looking to escape the city. Head to Commercial Street for shopping and dining, or even book a beautiful, historic home right on this main drag. Prefer some fun in the sun? Visit the beaches of the Cape Cod National Seashore—almost three quarters of Provincetown is preserved as a part of this park.

Our Top Restaurant Pick: Strangers & Saints

Our Top Activity Pick: Art’s Dune Tours

See all Provincetown vacation rentals on FlipKey!

Killington, Vermont (160 mi, 3 hrs)

Road trip ideas from Boston

Described by travelers as “an awesome mountain retreat!”, Killington boasts four seasons of non-stop adventure. Situated in the Green Mountains, Killington has some of the highest and most varied mountain terrain in the region. From hiking and biking during the summer to skiing and snowshoeing in the winter, the area’s natural beauty will steal your breath away. With FlipKey, you can stay near Killington Resort to be near all of the action, or find yourself in a country house off the beaten path. Wherever you choose, nothing beats a trip to this woodsy Vermont destination 160 miles northwest of Boston.

Our Top Restaurant Pick: PastaPot

Our Top Activity Pick: New Life Hiking Spa

See all Killington vacation rentals on FlipKey!

Lake George, New York (225 mi, 4 hrs)

Road trip ideas from Boston

This 32-mile long “Queen of American Lakes” offers lots of activities, perfect for stretching your legs after a long car ride. Navigate the trails at Prospect Mountain, hit the links at Top of the World Golf Resort, or go parasailing over Lake George, legs dangling freely in the air. Rent a cozy cottage right on the lake for ultimate convenience, or choose an away-from-it-all log home for total relaxation. Whichever you pick, you’re sure to enjoy a weekend of outdoor recreation in New York’s scenic Adirondack region.

Our Top Restaurant Pick: Bistro LeRoux

Our Top Activity Pick: Parasailing Adventures

See all Lake George vacation rentals on FlipKey!

Jersey Shore, New Jersey (295 mi, 5 hrs)

Rent a beach home along the Jersey Shore.

No matter which beach town or seaside village along the Jersey Shore you make home, New Jersey’s sweeping coastline is well worth the car journey. The region spans from Sandy Hook in the north to Cape May Point in the south, with about 140 miles of sandy beaches and swaying dunes in between. Want to win big in Atlantic City? No problem! Dreaming of warm waters and ocean breezes? It’s all here! Jersey Shore has something for everyone.

Our Top Restaurant Pick: The Shrimp Box

Our Top Activity Pick: Naval Air Station Wildwood Aviation Museum

See all Jersey Shore vacation rentals on FlipKey!

Top Road Trip Destinations from Boston

  • Plymouth, Massachusetts
  • Rockport, Massachusetts
  • Hampton, New Hampshire
  • Providence, Rhode Island
  • Ogunquit, Maine
  • Kennebunkport, Maine
  • Old Orchard Beach, Maine
  • Saco, Maine
  • Portland, Maine
  • Provincetown, Massachusetts
  • Killington, Vermont
  • Lake George, New York
  • Jersey Shore, New Jersey

Plan a vacation to America's best beer cities.

Thirsting for your next vacation, but not sure where to go? Why not visit one of the best beer cities in the country!

Best Beer Cities in America

From the quaint side streets of Bar Harbor to the bustling neighborhoods of downtown Seattle, we’ve narrowed it down to eight amazing beer cities truly worth raising a glass to. Each spot has top-notch breweries with extensive lists of IPAs, pale ales, porters, pilsners, and more on tap. If you can name it, you can taste it in these destinations. While we can’t cover all the great craft breweries, we’re featuring our favorite in each city, so that you can spend more time tasting than planning.

Better yet, each of these destinations has a variety of vacation rentals from FlipKey to fit every budget and travel style. Whether you rent a luxurious condo in the heart of the city or an away-from-it-all cottage by the beach, we guarantee you’ll love having a comfortable home to retreat to after a fun-filled day at the brewery (and/or night at the bar!).

Plenty of fridge space for your take-home growlers, too!

Boston, Massachusetts | Trillium Brewing Company

Trillium Brewery in Boston, MA

Historic landmarks, fiercely loyal sports fans, and lots of craft beers to choose from—a trip to Boston offers something for everyone. While well-known breweries like Sam Adams and Harpoon have helped put Boston on the map as one of the best beer cities in the country, Trillium Brewing Company has emerged as a local favorite. It’s a unique New England farmhouse-style brewery offering a variety of beers that satisfy every palate. This family-run spot is just off the beaten path in Boston’s Fort Point neighborhood, so make sure not to miss it!

Before sampling the city’s thriving nightlife, take time to discover Boston’s famed attractions. Follow the Freedom Trail’s red-brick path through the city, catch a baseball game at the iconic Fenway Park, or find a park bench and watch the swan boats glide by in the Boston Public Garden. Your days are sure to fly by in this fast-paced city.

See all Boston vacation rentals on FlipKey!

Oakland Park, Florida | Funky Buddha Brewery

Funky Buddha Brewery in Oakland Park, Florida

What better way to cool down and quench your thirst than by ordering an ice-cold glass of beer at Funky Buddha Brewery! Located in Oakland Park, this hip spot features tours of its funky brewhouse, a wide variety of bold craft beers, and a fabulous menu. Sample a Floridian Hefeweizen in the taproom, or fill up a growler of Eternal Summer to take home to your Oakland Park vacation home.

During your trip, venture just 15 minutes down the road to Fort Lauderdale where blue-green waters and world-class beaches await. Whether you swim in the shimmering Atlantic Ocean or shop on Las Olas Boulevard, this part of southern Florida will keep you busy from sun up until sun down.

See all Oakland Park vacation rentals on FlipKey!

Rapid City, South Dakota | Firehouse Brewing Company

Firehouse Brewing Company in Rapid City, South Dakota

Firehouse Brewing Company opened its doors in 1991 as South Dakota’s very first brew pub. The legendary spot, which is listed on the National Historic Register, has nine beers on tap at any given time, and there’s even an on-site winery for those who prefer a glass of red or white instead. Stay for a meal (and a live performance under the band-shell!), or pop into the taproom for a quick drink during your stay.

Beer fanatic or not, Rapid City is a fantastic destination to visit. It’s the ideal home base for travelers looking to tour the scenic Black Hills and the perfect spot if you’re simply looking to experience a taste of the Midwest.

See all Rapid City vacation rentals on FlipKey!

Minneapolis, Minnesota | Fulton Beer

Fulton Beer in Minneapolis, Minnesota

What started as a small brewing operation run out of a garage is today Fulton Beer, one of the best breweries in downtown Minneapolis. At the taproom, you can sip on a cold one just 38 feet from where it was brewed, or pick up a Sweet Child of Vine six pack to enjoy in the comfort of your rental. Whether you prefer hoppy IPAs or flavorful barleywines, there’s no shortage of bold brews to choose from at Fulton Beer.

It’d be impossible to talk about the best beer cities in the country without mentioning Minneapolis, but this Twin City is full of excitement. The Mall of America (just 15 minutes away) is an absolute must, while the city also boasts a thriving theater and arts scene. Perfect for weekend getaways or week-long vacations, Minneapolis is a superb destination to visit year-round.

See all Minneapolis vacation rentals on FlipKey!

Seattle, Washington | Fremont Brewing

Fremont Brewing Company in Seattle, Washington

Fremont Brewing is a family-owned Seattle brewery that’s been producing first-rate artisan beers for nearly 10 years. Here, brewing is done in small batches only using the finest local ingredients—so it’s no surprise that this hot spot makes Seattle one of the best beer cities in America. Sample pale ales, IPAs, oatmeal stouts, and more while you’re at Fremont Brewing.

Besides beer, it wouldn’t be a trip to Seattle without a stop at the original Starbucks for a brew of a different type. For a snack, head to Pike Place Market, a hub of mouthwatering eats and delicious scents. Book a private retreat on the water or a central apartment in the city, and make the most of your time in Seattle.

See all Seattle vacation rentals on FlipKey!

San Diego, California | Thorn Street Brewery

Thorn Street Brewery in San Diego, CA

As new breweries keep opening up, San Diego has quickly emerged as one of the best beer cities in America. But, one in particular continues to stand out among the rest: Thorn Street Brewery. This local watering hole is dog-friendly and boasts a lineup of rotating nightly food trucks that are the perfect complement to the vast selection of craft brews on tap. Stop in for a quick pint or kick back and relax with friends in the large, open taproom.

You can’t visit San Diego and spend all your time indoors, though. Swim in the Pacific at La Jolla Shores Park, wander around Balboa Park, or people watch from your rental’s beachfront patio—the possibilities are endless!

See all San Diego vacation rentals on FlipKey!

Boulder, Colorado | Avery Brewing Company

Avery Brewing Company, Boulder, CO

While Boulder is undoubtedly an ideal destination for families, you ought to consider this sophisticated Colorado city for an adults-only getaway, too! It’s home to the award-winning Avery Brewing Company, which offers 30 “thoroughly American at heart” beers on tap—at all times! From year-round beers like the Belgian-style White Rascal to seasonal favorites such as the peach-flavored Perzik Saison, you’re sure to find something that will quench your thirst.

Of course, Boulder also has plenty to do to help you burn off those beer calories! Explore the foothills of the Rocky Mountains, bike along the river, or stroll around the University of Colorado’s flagship campus during your trip.

See all Boulder vacation rentals on FlipKey!

Bar Harbor, Maine | Atlantic Brewing Company

Atlantic Brewing Company in Bar Harbor, ME

A quintessential New England beach town with some of the best beer in the region? You guessed it—we’re talking about Bar Harbor! It’s where you’ll find the Atlantic Brewing Company just minutes from the quaint cobblestone streets of downtown. Over the years, the brewery has grown from a small one-barrel operation to a 15 barrel-system that produces tasty pints of English-style beer.

Visit Bar Harbor for the beer, and stay for the salty air and pristine natural beauty. Sunbathing along the coast and strolling down the famous Shore Path are two or Bar Harbor’s simplest pleasures. Want to see more of the island? Head to Acadia National Park or hop in a kayak to discover this charming New England destination’s showstopping scenery.

See all Bar Harbor vacation rentals on FlipKey!

America’s Best Beer Cities for a Vacation

  • Oakland Park, Florida
  • Rapid City, South Dakota
  • Minneapolis, Minnesota
  • Seattle, Washington
  • San Diego, California
  • Boulder, Colorado
  • Boston, Massachusetts
  • Bar Harbor, Maine

Choose one of the best vacations for toddlers and plan your trip on FlipKey.

Best Vacations for Toddlers

The key to planning a worry-free vacation with toddlers is choosing the right destination. Whether it’s an exciting city brimming with hands-on activities, a peaceful beach, or a rural setting where kids can explore, it has to be a place where both the young and getting older can have fun (after all, it’s your vacation, too!).

To help you choose, we’ve hand-picked 10 of the best vacations for toddlers from coast to coast. From the action-packed streets of Washington, DC to the picturesque shores of San Diego, the places on our list make every curious toddler’s favorite question—”Why?”—easy to answer. We’ve even included our top pick for a kid-friendly attraction your little ones will love.

With more than 300,000 rentals to choose from on FlipKey, opt for a vacation home during your family getaway and benefit from extra space, free laundry, and a full kitchen to prepare meals for even the pickiest of eaters.

Captiva Island, Florida

Find the perfect rental for your family on FlipKey.

Captiva Island rests just off the coast of southwest Florida in the emerald waters of the Gulf of Mexico. It’s known for its shallow waters and gentle waves, which make it an ideal beach vacation spot for families with toddlers. With your little ones at your side, chase waves retreating into the ocean, build an enormous sandcastle, or comb the beach for colorful seashells—the possibilities are endless! Choose a beachfront condo with kid-friendly activities (think kite-making and coconut-painting) or book a vacation home with tons of space for a stress-free getaway in Captiva Island.

Top kid-friendly attraction: Sanibel Sea School

See all Captiva Island vacation rentals from FlipKey!

Pigeon Forge, Tennessee

Book a spacious cabin in Pigeon Forge.

With its small-town vibe and inviting atmosphere, one thing’s certain: you’re sure to feel at ease in Pigeon Forge (at least, while the kids aren’t testing your patience!). Situated in the heart of the Smoky Mountains, this outdoorsy destination is all about experiencing the Appalachian wilderness hands-on. In other words, it’s a toddler’s dream-come-true. Explore the dense forests on foot, bike along nature paths, or take a dip in the local swimming holes. If that’s not your thing, downtown Pigeon Forge boasts family-friendly theme parks, unique attractions, and the sounds of country music on almost every street corner, ensuring a good time is had by all.

Top kid-friendly attraction: The Coaster at Goats on the Roof

See all Pigeon Forge vacation rentals from FlipKey!

Stowe, Vermont

Play outdoors during a vacation to Vermont.

Located just miles from Smugglers Notch, one of Vermont’s largest state parks, Stowe boasts countless kid-friendly hikes, scenic byways, and undiscovered attractions. Translation: Stowe is the ultimate natural playground for toddlers. Let your children run free, climbing over twisted roots, playing hide-and-go-seek among the trees, and breathing in the fresh mountain air. Once everyone’s all tired out, retreat to your spacious cabin rental, and spend the evening cuddled on the couch watching movies and reading bedtime stories. Sometimes the best vacation for toddlers is one that involves minimal plans and a place to let loose.

Top kid-friendly attraction: Stowe Bowl

See all Stowe vacation rentals from FlipKey!

Orlando, Florida

Orlando best vacation for toddlers

It goes without saying that Orlando is one of the best vacations for toddlers. Home to the world-famous Disney theme parks, happiness fills the air here. Explore a lush, African savanna at Disney’s Animal Kingdom, stay cool at the Typhoon Lagoon Water Park, or watch your children’s eyes light up while hugging Mickey Mouse. The fun doesn’t have to end when you exit the park’s gates, though! Many Orlando vacation rentals bring the magic home with Disney-themed rooms, fabulous pools, and lots of space to play. Visit Orlando and even adults will feel like kids again!

Top kid-friendly attraction: Crayola Experience Orlando

See all Orlando vacation rentals from FlipKey!

Lake Ozark, Missouri

Lake Ozark, MO retreat

With miles of scenic lakefront, world-class boating, and a convenient location in the center of Missouri, Lake Ozark is a fabulous vacation spot for families, especially those with toddlers. Let the hours slip by swimming, strolling, or simply relaxing on the picturesque shores. For toddlers, there are endless things to do and no shortage of hiding spots for your inquisitive little one(s) to discover. At the end of the day, kick up your feet at your cabin rental, and watch the sunset over the water. Indoors and outdoors, your whole family will have fun in Lake Ozark!

Top kid-friendly attraction: Miner Mike’s Indoor Family Fun Center

See all Lake Ozark vacation rentals from FlipKey!

Washington, DC

With so much to do, Washington, DC is one of the best vacations for toddlers.

Washington, DC is loaded with captivating attractions your toddlers will love: the park-like National Zoo, several museums with interactive exhibits, and plenty of sprawling parks perfect for playing and picnicking, to name a few. Rent an apartment downtown or stay along the city’s outskirts—it’s easy to get around Washington, DC, even with toddlers in tow. Hop on the metro and breeze from destination to destination, or climb into a pedicab for an open-air ride through the city’s unique neighborhoods. Your wee ones will be awe-struck by the city’s massive monuments, historic buildings, and iconic landmarks looming in the skyline.

Top kid-friendly attraction: The International Spy Museum

See all Washington, DC vacation rentals from FlipKey!

San Diego, California

Beachside in San Diego, California.

San Diego is a laid-back beach town that’s fun to visit, with or without kids! When you arrive, make your first stop Balboa Park. It’s home to a large playground, nearly 20 museums, the San Diego Zoo, and so much more that will keep your little ones entertained for hours. Along the coast, soak up sun at Mission Beach or visit La Jolla Cove where seals and sea lions perch on the rocks all day long (cuteness overload!). FlipKey has plenty of San Diego rentals just steps from the beach, so you won’t have to tote your toddlers and beach toys too far for fun in the sun.

Top kid-friendly attraction: San Diego Children’s Discovery Museum

See all San Diego vacation rentals from FlipKey!

Lake Placid, New York

Boaters explore Lake Placid, NY

Travelers describe a vacation to Lake Placid as “a true Adirondack experience” and an “unbeatable, peaceful retreat.” Although it’s famous for being the site of the 1980 Winter Olympic Games and a hub for snow sports, this quiet city nestled in the mountains offers year-round activities the whole family will enjoy. During the summer, splash in the lake or sit by the fire pit as frogs croak and fireflies flit by. When winter rolls around, try skiing and ice skating, or climb Whiteface Mountain in the Cloudsplitter Gondola for sweeping views of Lake Placid. You’ll find this fabulous destination is as breathtakingly beautiful and full of adventure as it is toddler-friendly.

Top kid-friendly attraction: Whiteface Adventure Zone

See all Lake Placid vacation rentals from FlipKey!

Philadelphia, Pennsylvania

Philadelphia, Pennsylvania skyline

If you’ve never been to Philadelphia, you’ll quickly see why it’s a fabulous city and one of the best vacations for toddlers. From the massive Smith Memorial Playground & Playhouse to the Philadelphia Zoo, there’s plenty to keep your children amused for hours on end. With little ones constantly on the go, try not to miss the centuries of American history on display throughout the city—the Liberty Bell, Independence Hall, and Reading Terminal Market to name a few. Need another reason to visit Philadelphia? Sesame Place is just across the city line in Langhorne!

Top kid-friendly attraction: Please Touch Museum

See all Philadelphia vacation rentals from FlipKey!

Port Aransas, Texas

Port Aransas, TX is one of the best vacations for toddlers.

Fill your days in Port Aransas searching for seashells, fishing from the pier, and exploring the local nature reserves. The 18 miles of soft-sand beaches here provide a cushiony landing spot for toddlers still getting the hang of walking. Overhead, colorful Roseate Spoonbills and Reddish Egrets fly through the sky, while the sound of whooping cranes carries through the air delighting both young and young at heart. Make it easy on yourself by booking a rental right on the water so you won’t have to lug your beach gear too far. If you’re seeking an island retreat without a hefty price tag (you can rent a home for under $100 per night!) Port Aransas is the perfect place for you and your family.

Top kid-friendly attraction: Port Aransas Sandcastle Guy

See all Port Aransas vacation rentals from FlipKey!

Best Vacations for Families With Toddlers

  • Captiva Island, Florida
  • Pigeon Forge, Tennessee
  • Stowe, Vermont
  • Orlando, Florida
  • Lake Ozark, Missouri
  • Washington, DC
  • San Diego, California
  • Lake Placid, New York
  • Philadelphia, Pennsylvania
  • Port Aransas, Texas

From sugar-white sands and cerulean seas to thrilling adventures and fruity rum punches, the Caribbean is a tried-and-tested destination for relaxation. Now that school’s out for the summer, treat your family to the ultimate island getaway.

To make your trip even more enjoyable, consider staying in a FlipKey vacation rental. It’s no surprise that vacation homes are ideal for families—the extra living space, a full kitchen, and private outdoor area, plus amenities like laundry or a grill.

We’ve rounded up nine Caribbean destinations your family will love, each boasting some of the best vacation rental guest review scores in all of the Caribbean. From the mountains of St. Lucia to the sun-kissed shores of Turks & Caicos, choose a rental in one of these tropical hot spots and enjoy an authentic island experience.

Ratings are based on the lifetime average vacation rental review score for that destination (for stays during summer months), according to TripAdvisor reviewers. FlipKey is a subsidiary of TripAdvisor. 

1. Cayman Brac, Cayman Islands

A pool overlooks the beach in Cayman Brac, Cayman Islands.

Average Vacation Rental Rating: 4.96/5.00

“Peace and tranquility by the sea. Everything you need, and some things you didn’t know you needed, are available in this cottage.” – FlipKey Traveler

Ringed by silky sands and blue-green waters, Cayman Brac is an island paradise situated in the Caribbean Sea. Here, you can slip into relaxation mode while lounging along the 12 miles of golden beaches, or explore the rocky bluffs and pockets of caves lining the shore. Venture off the beaten path to discover the island’s natural beauty, or plunge into the surrounding sea for spectacular diving. Known for its stunning scenery and laid-back beach vibes, one thing’s certain: chilling with your family in Cayman Brac will never get old.

See all rentals in Cayman Brac from FlipKey!

2. Marigot Bay, St. Lucia

Sit on the balcony overlooking Marigot Bay in St. Lucia.

Average Vacation Rental Rating: 4.93/5.00

“Perfect place in Marigot Bay. We kept pinching ourselves as we stayed in this clean, light, beautiful apartment overlooking the bay.” – FlipKey Traveler

Home to the legendary Pitons and lush Pigeon Island National Park, St. Lucia is one of the most beautiful and mountainous islands in the Caribbean. Wake to the sound of birds chirping outside your window and ease into your day on the balcony of your Marigot Bay rental. When you’re ready for an adventure, drive into the depths of the La Soufrière volcano past steaming hot springs and therapeutic mud baths, or hop in a water taxi to explore the island’s secrets. Marigot Bay is perfect for families looking to add an unforgettable excursion (or two!) to their Caribbean getaway.

See all rentals in Marigot Bay from FlipKey!

3. East End, St. Thomas

Kayaks sit on the beach in East End, St. Thomas.

Average Vacation Rental Rating: 4.87/5.00

“Everything was perfect! We are beach sloths and seafood piggies and this was the best condo for our family at an unbelievably affordable price.” – FlipKey Traveler

Dig your toes into the sand and let your worries wash away while on vacation in St. Thomas’s picturesque East End. This part of the island is where you’ll find Red Hook—a delightful community characterized by its red-tiled roof homes—as well as a bustling port that makes island hopping a cinch. Prefer to relax? Unfurl your towel at Sapphire Beach and enjoy a day of sunbathing and snorkeling with your family. No matter how you choose to spend your time, East End is a top-rated Caribbean destination that won’t disappoint!

See all rentals in East End from FlipKey!

4. Bequia, St. Vincent and the Grenadines

The view from a vacation rental in Bequia.

Average Vacation Rental Rating: 4.81/5.00

“The lovely environment of the villa with its lovely pool and outdoor areas provided a welcome respite and gathering place for our family.” – FlipKey Traveler

Wide, sandy beaches, crystal clear waters, and dazzling coral reefs grace the shores of Bequia, a lush island in the Grenadines. At only seven square miles, everyone knows everyone here, and it’s the perfect destination for travelers searching for a friendly atmosphere and inviting, small-town feel. Lounge in the sun at Princess Margaret Beach or Lower Bay Beach, or go for a stroll around the village of Port Elizabeth—just don’t be startled by friendly chickens strutting at your feet. As the sun starts to fade on the horizon, head home to your waterfront rental, and pass the time guessing which celebrities are aboard the massive yachts anchored out your window in Admiralty Bay.

See all rentals in Bequia from FlipKey!

5. Providenciales, Turks and Caicos

Hammock in Turks and Caicos.

Average Vacation Rental Rating: 4.80/5.00

“Perfect piece of paradise on Chalk Sound. Our 3-generation family was so happy… Every night was perfect in its own way.” – FlipKey Traveler

In Providenciales (“Provo” to the locals), enjoy a breathtaking panorama of blue skies and turquoise surf, right from your seat in the sand. This sun-drenched destination is home to the TripAdvisor Travelers’ Choice award-winning beach, Grace Bay, and is the ultimate place to escape the day-to-day. Dive into the crystal clear waters and explore the miles of coral reef just offshore, or start happy hour early and indulge in some of the island’s signature Rum Punch.

See all rentals in Providenciales from FlipKey!

6. Willemstad, Curaçao

Plan a trip to Willemstad, Curacao.

Average Vacation Rental Rating: 4.70/5.00

“Loved it!!!!! The whole trip was awesome. Right from the booking to the day we went home!” – FlipKey Traveler

The capital of Curaçao, Willemstad boasts a lively downtown that bursts with colorful colonial architecture, Dutch-inspired landmarks, and a vast array of beach attractions. Float down the city’s winding waterways or stroll down the streets of the Punda and Otrobanda neighborhoods, taking in all that makes Willemstad a UNESCO World Heritage Site. When you’re not browsing the packed art galleries or sampling cocktails mixed with the island’s famed Blue Curaçao, retreat to your pastel-colored condo to relax on your balcony. From its historic charm and beautiful beaches to its year-round flawless weather, it’s no surprise that Willemstad ranks on our list of top-rated Caribbean destinations.

See all rentals in Willemstad from FlipKey!

7. Punta Cana, Dominican Republic

Book a villa in Punta Cana, Dominican Republic.

Average Vacation Rental Rating: 4.65/5.00

“Sooo AMAZING that we requested to book a second stay <24 hours after returning home!!!” – FlipKey Traveler

As soon as you set foot in Punta Cana, you’ll be on island time. Experience the thrill of zip-lining through the jungle, discover the hidden lagoons of Hoyo Azul, or dive into a colorful new world under the water. Up for a challenge? Punta Cana has several world-class golf courses with rolling fairways and contoured greens that are sure to provide a golf outing unlike any other. Whether you spend your days rocking in the hammock at your rental or playing in the surf, you’ll leave Punta Cana absolutely rejuvenated.

See all rentals in Punta Cana from FlipKey!

8. Ocho Rios, Jamaica

Stay near the beach in Ocho Rios, Jamaica.

Average Vacation Rental Rating: 4.61/5.00

“The best time ever!!! Maurice (the caretaker) had that reggae music pumping for us and we loved it…dancing and singing around the villa! Yea Mon!” – FlipKey Traveler

Leaping from Blue Hole waterfall, floating down the White River, and swimming at Bamboo Beach… there are so many ways to make a splash in Ocho Rios. From thrilling adventures to laid-back happy hours, this island oasis will keep you busy for days on end. After a day of fun in the sun, let your mind wander as the breeze carries the rhythmic sound of steel drums through the air. Book a sprawling beach villa right on the water and start counting down the days until your blissful beach getaway.

See all rentals in Ocho Rios from FlipKey!

9. Nassau, Bahamas

Rent a waterfront home in Nassau, Bahamas.

Average Vacation Rental Rating: 4.58/5.00

“Our experience was A+! We absolutely LOVED the property, the town and the people we worked with.” – FlipKey Traveler

Among the top beach spots in the world, Nassau is the picture of tranquility. Here you’ll find calm, turquoise waters lapping the pristine shores, refreshing Sky Juice (a local favorite) flowing freely, and delectable conch fritters always available. In other words, Nassau offers the ultimate recipe for vacation perfection. Cut through the waves in a catamaran, snorkel with a school of fish, or laze under the sun—the possibilities are endless at this top-rated Caribbean destination!

See all rentals in Nassau from FlipKey!

Best Caribbean Destinations To Rent A Vacation Home

  1. Cayman Brac, Cayman Islands
  2. Marigot Bay, St. Lucia
  3. East End, St. Thomas
  4. Bequia, St. Vincent and the Grenadines
  5. Providenciales, Turks and Caicos
  6. Willemstad, Curaçao
  7. Punta Cana, Dominican Republic
  8. Ocho Rios, Jamaica
  9. Nassau, Bahamas

Whether you’re celebrating a stellar report card or embracing warmer weather, summer is the perfect time for a fun-filled family vacation. So, if you’re in need of a little inspiration, we’re here to help with our list of 12 summer vacation ideas, tailored to your family’s interests. Relax at the beach, explore a new city, or climb a mountain—these trips are sure to please the whole gang!

Choose from more than 300,000 rentals on FlipKey, and enjoy all the comforts of home during your family summer vacation.

Artsy Vacation | Grand Rapids, Michigan

Grand Rapids is one of the most popular summer vacation ideas for families that love art.

Your family: scours the web for the latest art gallery openings and appreciates art in all its forms.

The destination: Home to one of the world’s 100 most-visited art museums, Grand Rapids is one of the best summer vacation ideas for families that love art. Mornings here are best spent discovering life-size works of art in the city’s renowned sculpture park. Save your afternoons for experiencing the flourishing arts and cultural scene downtown. Pop in and out of art museums (admission ranges from free to $10), or visit a local furniture shop and discover the original artistry that put Grand Rapids on the map.

FlipKey family favorites nearby…

Grand Rapids Art Museum | 101 Monroe Center St NW, Grand Rapids, Michigan

LaFontsee Galleries | 833 Lake Dr SE, Grand Rapids, Michigan

Bagger Dave’s Burger Tavern | 2190 East Beltline Ave. NE, Grand Rapids, MI 49525

See all rentals in Grand Rapids

Beach Vacation | Hilton Head, South Carolina

Hilton is a hot spot for family summer vacations.

Your family: lives for days at the beach and looks sun-kissed all summer long.

The destination: Families seeking a trip filled with sun, sand and surf will find Hilton Head to be an idyllic vacation spot. Relax on a wide, windswept beach or recruit other families for a game of volleyball on the sand. From oceanfront homes, steps from the water, to cozy apartments in the heart of town, your family will love the convenience (and affordability!) of having an entire rental all to yourself. In Hilton Head, family fun goes hand in hand with sun-dappled days and golden beaches.

FlipKey family favorites nearby…

Freedom Boat Club | 1 Waterway Ln, Hilton Head Island, SC 29926

H2O Sports | 149 Lighthouse Rd., Hilton Head Island, SC 29928

Hudson’s Seafood House on the Docks | 1 Hudson Road, Hilton Head Island, SC 29926

See all rentals in Hilton Head

Musical Vacation | Nashville, Tennessee

Find a rental in Nashville and enjoy all the city's musical attractions.

Your family: are enthusiastic gig-goers who love a good sing-along.

The destination: There’s no better place for music-loving families than Nashville. Nicknamed Music City, you’ll find everything from up-and-coming artists and mainstream music-makers to museums and landmarks that tell the history of the music industry here. Dance your way down Lower Broadway, world-famous for its non-stop live entertainment and countless honky-tonks, or take the family to a show at the renowned Grand Old Opry. For a toe-tapping good time on your summer family vacation this summer, Nashville is the obvious choice.

FlipKey family favorites nearby…

Fanny’s House of Music | 1101 Holly St Nashville, Tennessee, TN 37206

The Musician’s Hall of Fame and Museum | 401 Gay St Nashville, Tennessee, TN 37219

Captain D’s | Multiple

See all rentals in Nashville

Entertainment Vacation | Omaha, Nebraska

Your family: love theater productions, movies, educational programming, you name it—your family enjoys it all!

The destination: Often overlooked when it comes to summer vacation ideas for families, Omaha offers fun for all ages. Set aside time to explore the cobblestone streets of the Old Market—Omaha’s historic entertainment district—where you can enjoy captivating events or simply be entertained by people watching. Other entertainment options include catching a performance at the community playhouse or splash around at one of Omaha’s water parks. If you’re stumped in terms of summer family vacation ideas, we urge you to consider this hidden gem!

FlipKey family favorites nearby…

SkateDaze | 3616 S 132nd St, Omaha, NE 68144

Film Streams | 1340 Mike Fahey St., Omaha, NE 68102

Block 16 | 1611 Farnam St., Omaha, Nebraska 68102

See all rentals in Omaha

Sporty Vacation | Dallas, Texas

Dallas, Texas

Your family: cheers for their home team, no matter the sport and turns everything into a competition.

The destination: As far as summer vacation ideas for families that love sport goes, Dallas is hard to beat. Here, you’ll find several professional sports teams and loads of attractions to bring out your competitive side. Cheer on the Texas Rangers at Globe Life Park, challenge each other to a round of golf, or explore the city via a running tour. When you’re not touring Cowboys Stadium or playing at one of the many parks, make yourself at home on the front porch of your Dallas vacation rental.

FlipKey family favorites nearby…

TopGolf Dallas | 8787 Park Ln, Dallas, TX 75231

Nick’s Sports Cards & Memorabilia | 7522 Campbell Rd. Suite 119, Dallas, TX 75248

Lockhart Smokehouse | 400 W Davis St., Dallas, TX 75208

See all rentals in Dallas

Cultural Vacation | Savannah, Georgia

Book a rental in Savannah for your family summer vacation.

Your family: makes it a priority to learn something new about every place you visit.

The destination: For families that love to soak up the culture during their stay, Savannah is ideal. From centuries-old antebellum mansions to hauntingly beautiful cemeteries, stroll through the city and you’re sure to uncover the local culture and history. Savannah is known for embracing its cultural roots, displaying art and historic exhibits at the city’s 30+ museums. Linger at Forsyth Park, imagining all the famous people to have stood there before you, or enjoy some Savannah home cooking at one of the many award-winning restaurants.

FlipKey family favorites nearby…

Kayak Kafe Midtown | 5002 Paulsen St., Savannah, GA 31405

Juliette Gordon Low Birthplace | 10 E Oglethorpe Ave, Savannah, GA 31401

Georgia Historical Society | 501 Whitaker St, Savannah, GA 31401

See all rentals in Savannah

Adventure Vacation | Sedona, Arizona

Keep Sedona in mind when thinking of summer vacation ideas for families.

Your family: can’t say no to anything that gets the adrenaline pumping and would jump out of a plane for fun.

The destination: Known for its fiery red rock canyons, countless nature trails and abundance of wildlife, Sedona is a vacation paradise for adventure-seeking travelers. It’s situated right in the middle of the Arizona desert and is one of our favorite summer vacation ideas for families looking for more daring experiences. Whether it’s whooshing down a mountain on a bicycle or turning a casual hike into an outdoor adventure, there’s no limit to the potential for thrills in Sedona.

FlipKey family favorites nearby…

Red Rock Balloon Adventures | 273 N Hwy 89A, Suite M & N, Sedona, AZ 86336

Arizona ATV Adventures | 1185 W Highway 89A, Sedona, AZ 86336

Pisa Lisa | Coconino National Forest, 2245 AZ-89A, Sedona, AZ 86336

See all rentals in Sedona

Laid-back Vacation | Hampton, Virginia

Find a vacation home in Hampton, VA to relax.

Your family: believes that no plan is the best plan and always goes with the flow.

The destination: Toss your itinerary out the window and lose track of time in Hampton. It’s hard to beat this destination if you’re simply looking to relax and spend time together as a family during your summer vacation. Hit the beach for a blissful day in the sun or roam around one of the local parks. In addition to its leisure activities, Hampton is hailed as a leader in the pursuit of aeronautics and space exploration. Combine relaxation and education by touring local specialty museums dedicated to the city’s contributions to science.

FlipKey family favorites nearby…

Fort Monroe at Old Point Comfort | 20 Ingalls Rd., Fort Monroe, VA 23651

Virginia War Museum | 9285 Warwick Blvd., Newport News, VA 23607

Mission BBQ | 2035 Von Schilling Dr, Hampton, VA 23666

See all rentals in Hampton

Active Vacation | Boulder, Colorado

Add Boulder to your list of vacation ideas for families that love to stay active.

Your family: finds it impossible to sit still and is always on the move.

The destination: You can do it all in Boulder. Trek through pine forests, stroll across fields of wildflowers, climb to snow-capped peaks of majestic mountains and still make it back to your vacation rental by dinnertime. The city is filled with opportunities for outdoor recreation and the surrounding 30,000 acres of pristine land beg to be explored. Whether your family is in peak physical condition or simply choosing to explore the outdoors, Boulder is ideal for travelers who don’t want to slow down on vacation.

FlipKey family favorites nearby…

Boulder Rock Club | 2829 Mapleton Avenue, Boulder, CO 80301

Fair Winds Hot Air Balloon Flights | 10538 Arapahoe Rd., Lafayette, CO 80026

Foolish Craig’s Cafe | 1611 Pearl St., Boulder, CO 80302

See all rentals in Boulder

Foodie Vacation | Portland, Maine

Portland, ME is a favorite vacation destination among foodie families.

Your family: will travel for food and can’t say no to dinner at the hottest new restaurant.

The destination: Delicious eats and one-of-a-kind microbreweries are all within reach in Portland. While this family summer vacation destination has long been revered for its fresh-off-the-boat seafood, today, its restaurant scene is famous for all types of cuisine. Head downtown where restaurants dot the cobblestone streets, or stroll along the coastline until you stumble upon a hole-in-the-wall seafood shack. Prefer to earn your meal? Experience what life is like for a lobsterman in Maine, hauling in traps and bringing home your fresh catch to cook for dinner at your vacation rental. Don’t forget to bring your appetite when you visit Portland!

FlipKey family favorites nearby…

Boda | 671 Congress St.,Portland, ME 04101

Hot Suppa | 703 Congress St., Portland, ME 04102

Portland Lobster Company | 180 Commercial St., Portland, ME 04101

See all rentals in Portland

Nature Vacation | Clarksville, Virginia

Clarksville is one of the best summer vacation ideas for families that love nature.

Your family: loves the outdoors and any chance to be surrounded by nature.

The destination: Clarksville has everything a nature enthusiast craves from beautiful state parks, grand lakes and sprawling farms to lush vineyards. Families will love this summer vacation spot because children can play carefree outside while adults sneak a nap under the shade of an old oak tree. Wake up in your cabin to the sound of birds chirping, or rent a lake house and and be lulled to sleep by the soothing sound of water rippling outside your window. Walk, swim, float, or fish on vacation in Clarksville—the possibilities are endless!

FlipKey family favorites nearby…

Three Sisters of Shiney Rock Winery | 5484 Shiney Rock Rd., Clarksville, VA 23927

Occoneechee State Park | 1192 Occoneechee Park Rd., Clarksville, VA 23927

The Lamplighter Restaurant & Candlelight Lounge | 201 Virginia Ave., Clarksville, VA 23927

See all rentals in Clarksville

Vacation with Young Kids: Anaheim, California

Anaheim is one of the best summer vacation ideas for families with young children.

Your family: is about to book your first summer vacation as a family, planning your itinerary around nap time, or course.

The destination: Its proximity to Disneyland makes Anaheim a top choice when it comes to vacation ideas for families with young children. The city’s beloved theme park boasts fun with Mickey and Minnie for the little ones and thrilling rides for the adults. Or trade your Mickey ears for a baseball cap and catch a game at Angel Stadium. Cheap tickets and kid-friendly foods (hello, helmet sundae!) make it an excellent evening activity for the young and young-at-heart. We bet your kids will be begging to move to Anaheim after visiting this popular, family-friendly city.

FlipKey family favorites nearby…

Seascape Kids Fun | 4771 E Hunter Ave., Anaheim, California, CA 92807

Bowers Museum | 2002 N Main St., Santa Ana, California

The Pizza Press | 1700 S Harbor Blvd, Anaheim, CA 92802

See all rentals in Anaheim

Looking for more summer travel inspiration? Check out the best summer vacations to fit your budget from our friends at TripAdvisor!

Summer is the perfect season to explore the great outdoors.

With warmer weather on the way, travelers are being coaxed out of hibernation to enjoy the great outdoors. Sandy beaches and swaying palm trees might sound tempting, but consider trading your sandals for hiking boots this summer and plan a trip to the mountains instead.

So where should you go?! We’ve rounded up some of the best spots to rent a FlipKey home, breathe in fresh air, and enjoy sunshine away from the beach. Best known for winter sports, in the summer the charming mountains towns on our list offer action-packed activities, welcoming locals, and a fun-filled atmosphere during the off-season.

North Conway, New Hampshire

North Conway on a warm, sunny day.

“Our favorite part after going on adventures during the day was to retreat back to the chalet and sit around the fire pit as a family and enjoy the beauty of Cathedral Ledge right from our backyard.” – FlipKey Traveler

Known as the home of Cranmore Mountain Resort, North Conway is a popular place to visit when summer rolls around. Situated in New Hampshire’s Mount Washington Valley, this town boasts majestic mountains and trickling streams that instill an instant appreciation for Mother Nature. Must-dos include following the Black Cap Hiking Trail past fields of flowers, summiting Mt. Washington, and driving along the Kancamagus Highway. Whether you choose to fill your days rock climbing and hiking or shopping and strolling, there’s never a dull moment during a North Conway summer.

Eat: Delaney’s | 2966 White Mountain Highway, North Conway, NH 03860

Play: Mystery NH | 32 Mountain Valley Boulevard, North Conway, NH, USA 03860

See: Tuckerman Brewing Company | 66 Hobbs St Conway, New Hampshire, NH 03818

Stay: See all rentals in North Conway

Whitefish, Montana

Summer activities abound in Whitefish.

“We did it all! Went to Glacier National Park, enjoyed Big Mountain, toured the town and relaxed in the hot tub!” – FlipKey Traveler

Considered the gateway to Glacier National Park, Whitefish is a small town with big adventures. Soar above the slopes of Whitefish Mountain Resort on a zip line tour or maneuver from tree to tree at the resort’s obstacle course. Ready to relax? Soak up the beauty of the surrounding Rocky Mountains while sitting on your vacation rental’s back deck. Nature lover or extreme sports enthusiast, spectacular summer activities abound in Whitefish.

Eat: The Buffalo Cafe | 514 3rd St, Whitefish, MT 59937

Play: Whitefish Bike Retreat | 855 Beaver Lake Rd, Whitefish, MT 59937

See: Flyboard of Montana | Lakeside Blvd, Whitefish, MT 59937

Stay: See all rentals in Whitefish

Mount Shasta, California

There is lots to do in Mount Shasta after the snow disappears.

“We always seem to have the perfect mix of activities and quiet times, and we come away from our vacation with renewed energy.” – FlipKey Traveler

It’s no surprise that visitors continue to fall in love with Mount Shasta long after the snow has melted. Situated at the end of the Cascade Range, the city’s namesake volcano is the main draw. Mount Shasta’s spectacular hiking trails are a delight, whether you have just 15 minutes or a whole day to explore them—keep an eye out to glimpse the local wildlife and admire the unique volcanic rocks. Prefer something more laid-back? Cast your fishing line into the clear waters of the high mountain lakes for the ultimate peaceful day in Northern California.

Eat: Black Bear Diner | 401 W. Lake St, Mt. Shasta, CA  96067

Play: Alpen Cellars | 2000 E Fork Rd, Trinity Center, CA 96091

See: Turtle Bay Exploration | 844 Sundial Bridge Dr, Redding, CA 96001

Stay: See all rentals in Mount Shasta

Stowe, Vermont

The views of Stowe are spectacular during the summer months.

“A perfect base to either hunker down and read around the wood burning stove or use as a base to explore the nearby hiking or the quaint town of Stowe.” – FlipKey Traveler

During the summer, the snowy-white mountains of Stowe turn a brilliant green and the area buzzes with life. This classic New England resort town is home to premier golf courses, scenic hiking trails, and endless adventures. Make the trek to the top of Mt. Mansfield—Vermont’s highest peak—for panoramic Green Mountain views. The region’s warm summer days provide ample opportunities to explore, while cool evenings allow for time gathered around a bonfire in the comfort of your FlipKey rental.

Eat: Piecasso Pizzeria & Lounge | 1899 Mountain Rd, Stowe, Vermont, VT 05672

Play: ArborTrek Canopy Adventures | 1239 Edward Rd, Jeffersonville, VT 05464

See: Idletyme Brewing Company | 1859 Mountain Rd, Stowe, VT 05672

Stay: See all rentals in Stowe

Sun Valley, Idaho

Explore Sun Valley during the off-season this summer.

“Our extended family had a wonderful week viewing the nearby mountains through a frame of golden aspen trees.” – FlipKey Traveler

Adventure never goes out of season in Sun Valley. With its striking setting and abundance of outdoor recreation activities, this mountain town in Central Idaho is ideal for a summer escape. Climb aboard a gondola and ride to the top of Bald Mountain for unparalleled views of the Rockies, or brave the rapids of the Salmon River on a guided rafting tour. Want everything at your fingertips? Book a condo rental near Sun Valley Resort and you’ll be where most of the action takes place.

Eat: Despo’s Mexican Restaurant | 211 Fourth St, Ketchum, ID 83340

Play: Zenergy Health Club and Spa | 245 Raven Rd, Ketchum, ID 83340

See: Sawtooth Brewery | 631 Warm Springs Rd, Ketchum, ID 83340

Stay: See all rentals in Sun Valley

Winter Park, Colorado

Discover all that Winter Park has to offer once the snow melts.

“Perfect place for a relaxing and FUN mountain getaway.” – FlipKey Traveler

Home of Winter Park Resort, this winter-playground-turned- summer-adventure-park has a lot to offer outdoor enthusiasts once the snow disappears. Make yourself at home in a cozy Winter Park cabin rental then head out to tackle the varied mountain terrain on foot or via bicycle. When you’re not enjoying breathtaking views from the top of the mountain, join a horseback riding tour or take your summer vacay to new heights on a hot air balloon ride. Don’t wait until winter returns to visit this charming mountain town!

Eat: The Ditch on 40 | 78941 US-40, Winter Park, CO 80482

Play: Mad Adventures | 78941 US-40, Winter Park, CO 80482

See: Grand Adventure Balloon Tours | 220 County Rd 522, Fraser, CO 80442

Stay: See all rentals in Winter Park

Have you spent the first days of spring waiting for pricey flights to the Caribbean to drop? Whether your heart’s set on a dreamy beach vacay or an exciting urban getaway, you don’t have to break the bank—or leave the country—to enjoy an amazing spring vacation.

Based on the median weekly rate for a two bedroom rental on FlipKey, we’re highlighting some of the most affordable spring vacation destinations in America and the must-dos in each city. From the shores of Cape Cod to the desert landscape of Palm Springs, here are some of the best places to celebrate the arrival of spring.

Boise, Idaho: $594/week

Rent a whole home in Boise for an affordable spring vacation.

With the majestic Rocky Mountains looming beyond the city limits and over 190 miles of trails to explore, Boise packs lots of punch for the nature-loving traveler. Climb the hill at Camel’s Back Park for great views of Southern Boise or take it easy on a stroll through the Idaho Botanical Garden. Had your fill of the outdoors? Boise’s varied museums and plentiful attractions will captivate all interests. However you choose to spend your time, Spring is the perfect season to enjoy all the city has to offer—before the dry summer heat sets in!

Eat: Boise Fry Company | Multiple locations in Boise

Play: Idaho Botanical Garden | 2355 Old Penitentiary Road, Boise, Idaho 83712

See: The World Center for Birds of Prey | 5668 West Flying Hawk Lane, Boise, Idaho 83709

Stay: See all rentals in Boise

Albuquerque, New Mexico: $597/week

Choose an adobe-style vacation home in Albuquerque for a spring getaway.

There are few places to experience the authentic Southwest quite like Albuquerque. With its fiery desert landscape, mouthwatering New Mexican cuisine, and unique multicultural heritage, this city is a magical escape for travelers of all ages. The city’s streets are lined with historic adobe homes and brick paths, while its clear, blue skies are dotted with colorful hot air balloons. Plentiful sunshine and mild temperatures add to this city’s appeal, making it one of the best affordable spring vacation spots on our list.

Eat: Vinaigrette | 1828 Central Ave. SW, Albuquerque, NM 87104

Play: ABQ Trolley | 800 Rio Grande Blvd. NW, Albuquerque, NM 87104

See: The National Museum of Nuclear Science and History | 601 Eubank Blvd. SE, Albuquerque, NM 87123

Stay: See all rentals in New Mexico

Chincoteague Island, Virginia: $650/week

A welcoming home in Chincoteague Island.

Chincoteague Island’s resident wild ponies have helped put this small Virginia town on the map. During the summer, they can be seen thundering down the golden beaches. But horses aren’t the only wildlife to be admired—the unspoiled beaches and lack of high-rises on Chincoteague Island make it a great place for bird watching, too. Escape to this affordable spring vacation destination for a breath of fresh air and a slower pace of life.

Eat: Island Creamery | 6243 Maddox Blvd. Chincoteague Island, VA 23336

Play: Chincoteague Cultural Alliance Markets | 6309 Church St, Chincoteague Island, VA 23336

See: Museum of Chincoteague Island | 7125 Maddox Blvd. Chincoteague Island, VA 23336

Stay: See all rentals in Chincoteague Island

Tacoma, Washington: $653/week

Downtown Tacoma, Washington is seen from above.

Situated in the Puget Sound area and easily accessible from Seattle, Tacoma is ideal for travelers who like to have lots of options. Ready to explore? Hop in the car and head to Mount Rainier National Park just a short drive away. Want to see what the downtown area has to offer? Tacoma is home to a vibrant community of artists and boasts many world-renowned museums and exhibits. Still, you might prefer to take in the scenic landscape from the comfort of your FlipKey rental like one reviewer who raved “being able to sit on the decking while you watch the sunset over the Olympic Mountain was beautiful.”

Eat: El Gaucho | 2119 Pacific Ave, Tacoma, WA 98402

Play: Five Mile Drive and Trails | 5400 N. Pearl St. Tacoma, WA 98407

See: Museum of Glass | 1801 Dock Street, Tacoma, Washington 98402

Stay: See all rentals in Tacoma

Tampa, Florida: $680/week

Book an affordable vacation rental for your stay in Tampa.

Whether you decide to book a modern condo downtown or a beach home nearby, Tampa is a popular spring vacation spot that won’t break the bank. Traveling with the entire family? Busch Gardens and The Florida Aquarium in Tampa Bay offer something exciting for every person in your group. Sports enthusiasts can catch a Tampa Bay Rays baseball game at the start of the season, while art lovers will be impressed by the city’s world-class museums. No matter what you do though, soak up some sun and enjoy Tampa’s waterfront location.

Eat: Datz | 2616 S MacDill Ave, Tampa, FL 33629

Play: Ulele Brewery | 1810 N Highland Ave, Tampa, FL 33602

See: Tampa Theatre | 711 N Franklin Street, Tampa, FL 33602

Stay: See all rentals in Tampa

Palm Springs, California: $688/week

Enjoy views of palm trees from your bedroom in Palm Springs.

Thanks to its year-round pleasant climate and abundance of golf courses, a spring vacation in Palm Springs never disappoints. Soak up sun by the pool at your FlipKey rental, hop on a bike to explore, or discover the beauty of the surrounding desert on foot. Rather stay cool? Relax at one of the many award-winning spas in Palm Springs or hit some of the nearby museums. Whatever you decide to do, don’t miss out on the chance to spend a week here during the spring months.

Eat: Workshop Kitchen + Bar | 800 N Palm Canyon Dr, Ste G, Palm Springs, California 92262

Play: Palm Springs Air Museum | 745 North Gene Autry Trail, Palm Springs, California 92262

See: Elvis Honeymoon Hideaway | 1350 Ladera Circle, Palm Springs CA 92262

Stay: See all rentals in Palm Springs

Dennis Port, Massachusetts: $800/week

A charming Dennis Port vacation rental awaits guests.

Visit Dennis Port during the spring before tourists flock here for the peak summer season. This charming Cape Cod town oozes charm with its cozy cottages, wooden boardwalks, and photographic beach views. From skipping stones on the glassy waters to shopping at the local general store, Dennis Port has everything you need (and more!) for a delightful vacation, without the stress of going over-budget.

Eat: Sundae School Ice Cream | 381 Lower County Road, Dennis Port, MA 02639

Play: The Improper Bostonian | 626 Main St, Dennis Port, MA 02639

See: Stage Stop Candy | 411 Main Street, Route 28 Dennisport, MA 02639

Stay: See all rentals in Dennis Port

Lake Harmony, Pennsylvania: $800/week

Boats are docked along Lake Harmony.

Tucked away in the Pocono Mountains, Lake Harmony is the perfect spot to welcome spring. The season brings the arrival of blooming daffodils and laurel blossoms, along with endless possibilities for outdoor recreation. Book a lakefront vacation home and wake up to sunrise over the water, or rent a cabin in the middle of the woods and truly escape it all. Whether you’re a hiker, biker, boater or botanist, we bet you’ll love this budget-friendly destination!

Eat: Piggy’s Restaurant | 91 N. Lake Drive, Lake Harmony, PA

Play: Yeti WaterSports | 100 Moseywood Rd, Lake Harmony, PA 18624

See: The Split Rock Country Club | 140 Wolf Hollow Run Road, Lake Harmony, PA 18624

Stay: See all rentals in Lake Harmony

Scottsdale, Arizona: $800/week

Scottsdale is an affordable spring vacation destinations for US travelers.

In Scottsdale, you can be touring the beautiful desert one minute, and wrapped in a cozy bathrobe at one of the many spas the next. Explore the McDowell Sonoran Preserve, which offers trails for hikers of all skill levels. If it’s been a rainy spring, you might even get lucky and see the desert in bloom! Head to Old Town Scottsdale for shopping or skip straight to the downtown area where you’ll find a buzzing restaurant and party scene.  This spirited Southwest city is full of possibilities, especially during the spring!

Eat: Virtu | 3701 N. Marshall Way, Scottsdale, AZ 85251

Play: OdySea Aquarium | 9500 E Via De Ventura, Suite A-100, Scottsdale, AZ 85256

See: Western Spirit: Scottsdale’s Museum of the West | 3830 N. Marshall Way, Scottsdale, AZ 85251

Stay: See all rentals in Scottsdale

Lake Ozark, Missouri: $863/week

Book a Lake Ozark vacation rental and enjoy dinner overlooking the water.

Nestled in the heart of Missouri, Lake Ozark is a premier lake town offering world-class boating, fishing, and shopping. Cast your line from the shore and hook a fish, hike the surrounding landscape, or take the boat over to Party Cove during your stay. Whether you’re planning a family getaway or booking a couple’s retreat, choose a FlipKey rental for an affordable spring vacation you’ll always remember.

Eat: Baxter’s Lakeside Grille | 2124 Bagnell Dam Blvd, Lake Ozark, MO 65049

Play: Ha Ha Tonka State Park | 1491 State Road D, Camdenton, MO 65020

See: Bridal Cave | 526 Bridal Cave Rd, Camdenton, MO 65020

Stay: See all rentals in Lake Ozark

It’s not time to hibernate just yet! With the cold bite of winter not set to arrive until December 21, now is the time to get outdoors and check those last few fall activities off your list.

From apple and pumpkin picking to navigating corn mazes, we’ve rounded up the top places in America to experience six classic fall activities. Each spot is renowned for its gorgeous scenery, family-friendly attractions, and most importantly its ability to provide a day of seasonal fun.

Book yourself a cozy vacation rental, pack the flannel, and make the most of the fall season before winter sets in.

Top places for apple picking:

Fresh apples hang from a tree in the orchard.

Carter Mountain Orchard | Charlottesville, VA

From mid-August until mid-December, Carter Mountain Orchard offers 16 different varieties of apples available for picking. Hike through the acres of orchards nestled in the mountains of Virginia, and fill your sack with a variety of apples, including Fuji, Golden Delicious, Granny Smith and Pink Lady.

Lyman Orchards | Middlefield, CT

Don’t let the enticing aroma of pies, cider and doughnuts from the Apple Barrel deter you from the fun of picking your own apples at Lyman Orchards. (Or, at least not until you’ve had your fill of picking for the day!) Lyman Orchards has been growing fruit on the same land along the Connecticut River for more than a century, so head here for a classic apple picking experience.

Red Apple Barn | Ellijay, GA

Peaches aren’t the only succulent fruit grown in Georgia. During the fall, apples hang from the trees and ripen for plucking at Red Apple Barn. The orchard opens for weekend apple picking in September and only closes in October once the trees are bare. Apple varieties available here include Gala, Honeycrisp and Red Delicious. Keep in mind that they ripen at different times during the season, so plan your trip ahead of time if you have a favorite.

Sky Top Orchard | Flat Rock, NC

Nestled in the mountains of North Carolina, Sky Top Orchard offers unparalleled panoramic views in addition to a long list of apple varieties. Work up an apple-tite exploring the grounds then taste lots of apple goods like freshly pressed cider and hot caramel apples. There is nothing quite like spending a fall day at Sky Top Orchard.

Terhune Orchards | Princeton, NJ

Apple picking is a highlight of fall at Terhune Orchards. The season brings bushels of pick-your-own fruit, and a walk through the orchard’s apple trees is the perfect way to disguise exercise as a fun activity. The aroma of baked goods from the Farm Store will tempt you inside to sample some fall treats before you leave.

Westwind Orchard | Accord, NY

Apples and fall go hand-in-hand at Westwind Orchard. From McIntosh to Cortland apples, many varieties are grown at this orchard and they’re available for picking from mid-August until they run out, typically in October. The fruits produced here are certified organic and absolutely delicious.

Top corn mazes to explore:

A sign announcing the corn maze where the farmer has cut a maze in his field of corn.

Mike’s Maze at Warner Farm | Sunderland, MA

For nearly 20 years, Mike’s Maze has been creating a challenging new corn maze for guests to explore every fall. When you’re not surrounded by towering cornstalks, you’ll enjoy breathtaking views of New England’s fall foliage during the day. Once the sun sets, bundle up and brave the corn maze under the cover of darkness. This nighttime attraction is known as “Mike’s at Night” and features varying levels of scary as you make your way through the maze.

Poppell Farms | Odum, GA

Boasting “a-maizing adventures” and “farmtastic family fun,” a trip to Poppell Farms is never disappointing. This year, its 10-acre corn maze has been custom-designed to feature Peanuts themes and characters in honor of the 50th anniversary of the television special It’s the Great Pumpkin, Charlie Brown. More than 30,000 visitors are expected to visit Poppell Farms this season.

Queens County Farm Museum | Floral Park, NY

From late-September through October, kids and adults alike flock to the Queens County Farm Museum to take on the challenge of making their way out of the corn maze. Begin by getting tips about finding clues and solving puzzles during “Stalk Talk,” and then venture into the maze to see how quickly you can escape. The theme of the maze this year is “The Big Apple.”

Sherman Farm | Center Conway, NH

The Maize at Sherman Farm features 12 acres of farm-related fun set in a sprawling maze of corn. Intricate designs, riddles and corn-themed games add to the challenge of making your way through the outdoor labyrinth. Admission is $10 and gives you access most activities throughout the farm.

Siegel’s Cottonwood Farm | Lockport, IL

The corn maze at Siegel’s Cottonwood Farms will test even the best sense of direction. It is spread out over 15 acres of land and offers visitors five miles of cornstalk-lined paths to choose from. The maze is open on weekends during the fall and the farm features an additional 30 seasonal attractions that make for a full day of fall activities.

Treinen Farm | Lodi, WI

Even the most skilled navigators will agree that the corn maze at Treinen Farm can be extremely disorienting. It’s made up of over six miles of winding paths and features clues for getting out of the maze along the way. As well as the reward of completing the maze, there are chances to win prizes if you find secret locations that aren’t shown on the map. Expect the maze to take anywhere from 45 minutes to two hours to complete.

Top fall hayrides:

Red tractor and hayride trailer at an orchard.

Donaldson Farms | Hackettstown, NJ

Set on hundreds of acres of land, Donaldson Farms features lots of fall attractions for the young and young-at-heart. One of the most popular attractions at the farm is its seasonal hayrides. Horses pull an open wagon full of visitors through the farmland of Hackettstown providing the perfect backdrop for fall photo-ops.

Miller’s Big Red Farms | Washington, MI

Every acre bursts of Miller’s Big Red Farms bursts with something delicious to discover. Take a hay ride past rows of apple trees and colorful pumpkin patches to inspire what you’ll do next at this charming farm.

Northern Star Farm | Trappe, PA

With a bale of hay as your seat, sit back and relax as a tractor pulls you around Northern Star Farm under the night sky. The hay ride typically lasts about 30 minutes before dropping guests off at a bonfire on the grounds. Warm up by the fire and trade stories over food and drink with other visitors.

Patterson Farm | Mount Ulla, NC

Patterson Farm offers many fall activities all with the aim of inspiring visitors to get outdoors and create memories on the farm. The tractor-pulled hayrides here are fun for all ages and take guests through fields and pumpkin patches on gorgeous fall days.

Smolak Farms | North Andover, MA

Sit back and relax on a scenic hay wagon ride at Smolak Farms. Choose a “hop-on hayride” during the day to take in the beautiful landscape of fir trees, beehives and fragrant fruit orchards, or purchase a ticket for a night ride for stargazing and fun at a nearby bonfire site. This fall, Smolak Farms also offers an Alice in Wonderland themed hayride that features a narration of the storybook on limited weekends.

Wolfe’s Neck Farm | Freeport, ME

On Saturdays and Sundays in October, Wolfe’s Neck Farm offers its guests hayrides out to its picturesque pumpkin patch. Climb into the back of its open-air wagon and relax as a tractor pulls you past the magnificent fall foliage.

Top spots for pumpkin picking:

Cropped shot of a couple tending to their pumpkin at a farm.

Curtis Orchard & Pumpkin Patch | Champaign, IL

Get lost in a sea of orange at Curtis Orchard & Pumpkin Patch. Guests can pick their own pumpkins straight off the vines from mid-September to early November. Whether you’re looking for a perfectly round orange pumpkin, a warty one, or pumpkins of blue and white varieties, you’ll find a huge assortment at this pumpkin patch.

Harris Hill Farm | New Milford, CT

Harris Hill Farm offers a pick-your-own pumpkin patch open to visitors on weekends during the month of October. The family-owned farm is one of the area’s premier pumpkin growers, specializing in both large and mini pumpkins, as well as a variety of other fall crops that include gourds, winter squash and Indian corn. With five acres of pumpkins, you’re sure to find the perfect pumpkin for your jack-o-lantern at Harris Hill Farm.

Jubilee Farm | Carnation, WA

Every October, Jubilee Farm welcomes guests to its pumpkin patch to celebrate another bountiful harvest. Admission is free and the farm takes pickers out to the pumpkin patch via hay ride at no cost. Explore the rows of plump pumpkins while sipping freshly-pressed cider at this community farm in the Seattle area.

Mitchell Farms | Collins, MS

The pumpkin patch has been a vital part of Mitchell Farms for more than a decade. Besides offering pumpkins galore, visit this farm for a weekend of fun fall activities. Favorites include taking a wagon ride tour of the land, getting lost in a corn maze, wandering through a field of sunflowers and climbing aboard the Pumpkin Express train.

Santa Rosa Pumpkin Patch | Santa Rosa, CA

Start a new fall family tradition pumpkin picking at the Santa Rosa Pumpkin Patch. Across a whopping eight acres of pumpkin picking grounds, you’ll find several unique varieties including Cinderella and ghost pumpkins. Purchase a wristband to gain entry to the patch and stroll along with one of the farm’s wagons in tow.

The Community Orchard | Fort Dodge, IA

While it’s known for its impressive apple orchard, The Community Orchard is also home to a magnificent pumpkin patch that features 12 different varieties. Ranging in size, shape and color, there is a pumpkin for every kid and kid-at-heart here. Head straight to the patch or board the Pumpkin Cruiser for a tour of the farm.

Top places for seasonal food and drink:

Homemade Sugared Apple Cider Donuts with Cinnamon

Cupcake Royale | Seattle, WA

Pumpkin works its way into some of Cupcake Royale’s most mouthwatering creations during the fall. One taste of this shop’s Pumpkin Maple cupcake and you’ll immediately feel transported to a charming pumpkin patch surrounded by colorful foliage. The batter is made with pumpkin from Stahlbush Island and the cream cheese frosting has just the right amount of maple.

Newport Storm by Coastal Extreme Brewing | Newport, RI

The pumpkin beer from Newport Storm by Coastal Brewing is equivalent to fall in a pint glass. The seasonal favorite “R.I.P. Pumpkin” boasts three pounds of pumpkin per keg, a mixture of cinnamon, nutmeg, ginger, allspice and cloves, as well a variety of other flavorful ingredients. Take a self-guided tour of the brewery before enjoying a tasting of seasonal brews.

Puritan & Company | Cambridge, MA

The apple cider doughnuts at Puritan & Company are a little known secret in Cambridge. They’re not on the daily menu, but ask for them during Sunday brunch during the fall and your taste buds will be delighted. They pair perfectly with a bubbly mimosa.

Rare Sweets | Washington, DC

You’re in for a treat when you visit Rare Sweets during the fall. The Apple & Fall Spice Cake is a season favorite that features a sweet vanilla cake with housemade apple butter and fall spice icing. It’s worth every extra calorie.

Three Brothers Bakery | Houston, TX

A taste of the Deep Dish Chocolate Fudge Pecan Pie from Three Brothers Bakery will have you starting a new fall tradition with your family. The pie is made from scratch and packed with delicious pecans, gooey fudge and a crumbly crust. Not a fan of nuts? Try the Pumpecapple piecake or “the Turducken of pie and cake”, which has three layers of fall sweetness.

Vermont Spirits | Quechee, VT

Two words sum up fall at this craft distillery: Maple Spirit. It’s made from fermented maple distilled in a copper pot still. The smooth spirit is then aged in Hungarian oak barrels for extra flavor until it takes on a warm amber color. You won’t taste anything like it!

Grilling three hotdogs on a portable grill with glowing charcoal briquettes and American football in the corner. The freshly mowed natural green turf provides space for the tailgate.

Every year more than 17 million spectators flock to stadiums around the country to cheer their favorite NFL teams on to victory…but that’s not all they do.

Tailgating has become a wildly popular tradition in many cities around the country. Stadium parking lots fill with carloads of fans, the smell of sausages fills the air and beers are poured and passed throughout the day. They offer a lively atmosphere and an energy that summons both camaraderie and friendly competition among those who participate.

With football season in full swing, we wanted to highlight the cities with the biggest tailgate where there’s as much fun happening off the field as there is inside the stadium’s gates.

Buffalo Bills | Orchard Park, NY

Buffalo Bills fans aren’t shy about their love for tailgating. Come rain, shine or snow, fans flood the stadium lots the very second they open, four hours before each game. The city’s famed Buffalo chicken wings feature heavily, as do “beef on weck” sandwiches (roast beef on kummelweck rolls). You won’t go hungry among the endless rows of cars surrounding New Era Field.

If you’ve brought your kids along for the game, the Buffalo Bills host a massive indoor tailgate as well. Located inside the ADPRO Sports Training Center, families can enjoy live entertainment, interactive games, prizes and a variety of concessions.

The stadium itself is located in Orchard Park, just a short drive from downtown Buffalo. Choose from vacation rentals in either city and you’ll have convenient access to New Era Field, so you can maximize your tailgating time. Make a weekend getaway out of your football pilgrimage to New York, though, and tour the Albright-Knox Art Gallery, check out Frank Lloyd Wright’s unique Martin House Complex, and stroll around the vibrant Elmwood Village.

Recover at a nearby vacation rental in Buffalo, NY

Green Bay Packers | Green Bay, WI

Lambeau Field stadium and sign in Green Bay, Wisconsin has some of the best tailgates in the NFL.

Lambeau Field stadium and sign in Green Bay, Wisconsin.

Whether you’re able to enjoy a crisp, sunny day in Wisconsin or you’re huddled around a grill for warmth, Green Bay Packers tailgates are among the best. It’s to be expected though when the team is community-owned; Packers devotees can purchase shares in the team, upping the stakes of their team pride…and tailgates. Bratwurst and cheese are some of the most popular foods you’ll find Packers fans enjoying.

Lambeau Field’s east parking lot is home to the Tundra Tailgate Zone, which offers all of the game day excitement within climate controlled tents. Expect live music, former players signing autographs, food and more. The best part? No game ticket required.

Green Bay does have things to do besides take in a Packers game, though. Get yourself psyched up for the game by visiting the Green Bay Packer Hall of Fame, with its interactive displays and historic team treasures. Other attractions worth checking out include the Neville Public Museum, the National Railroad Museum and the Heritage Hill State Historical Park. Rent a home in town that puts you in close proximity to Green Bay’s best attractions.

Choose your home base in Green Bay, WI

Philadelphia Eagles | Philadelphia, PA

Arrive at Lincoln Financial Field and you’ll immediately be greeted by a sea of fans decked out in midnight green, silver and black. Tailgating is allowed in parking lots that surround the stadium and they open five hours before kick off. After devouring the requisite Philly cheesesteak, wander over to the Wells Fargo Center parking lot to see The Football Shuttle, a school bus that’s been re-designed just for tailgating.

Tack on an extra day to your vacation after the Eagles’ game to recover at your Philadelphia rental or spend time exploring America’s historic city. There are many must-see attractions here, including the Liberty Bell and Independence Hall, where the Declaration of Independence and Constitution were signed. The Reading Terminal Market has something for everyone and the Philadelphia Museum of Art will amaze art-lovers.

Search for an urban escape in Philadelphia, PA

Cleveland Browns | Cleveland, OH

First Energy Stadium, home of the NFL Cleveland Browns.

First Energy Stadium, home of the NFL Cleveland Browns.

Despite the Browns’ record, the city’s fans take their tailgating seriously. The city comes together each week to cheer on its home team, and, as a result, the Cleveland Browns “Muni Lot” has become legendary for its enthusiastic tailgates. The parties take place across 16 acres of land with games, food and celebrations. Be on the lookout for a bus with a giant dog head on the front, affectionately known as the Tailgate Dawg.

One of the advantages to staying in a vacation home during your trip to Cleveland is access to a full kitchen. Stock up on hamburger patties and buns, beer and snacks the day before the game and organize everything at your rental before heading out. When packing for your weekend in Browns territory, make sure that all of your orange and brown apparel makes it into your suitcase. You don’t want to stand out as an opponent in a sea of Browns fans here.

Rest up for the weekend in your Cleveland, OH vacation home 

Houston Texans | Houston, Texas

The expression that “everything is bigger in Texas” certainly holds true for their tailgating scene. From brisket and burgers to deer and elk, you’ll find a variety of meat to enjoy at Texan tailgates. The lots open four hours before kickoff and parking is first-come, first-served. The local grocery store H-E-B sponsors the gameday tradition of naming the Tailgater of the Game, so make sure to prepare your finest barbecue and dips for a shot at bragging rights.

If you don’t need to be there four hours before the game starts, take the light rail train from Midtown to NRG Stadium. Trains run every 12 minutes and cost a nominal fee of $1.25 per ride. Just make sure to pack extra food and tailgate supplies so you can persuade someone with a parking spot to let you join.

Book a Houston rental in advance since the city is flooded with Texan fans that pour into NRG Stadium’s more than 72,000 seats each game. In addition to having the allure of NFL football games, the fall months are ideal for visiting Houston because temperatures drop slightly at this time of year. Expect to enjoy daytime highs in the low-80s, or pack a light jacket if you’re going to an evening game when temperatures might dip into the 50s.

Search for a rental near the stadium in Houston, TX

Pittsburgh Steelers | Pittsburgh, PA

Three people kayaking in the Allegheny River in front of Heinz Field, home of the Pittsburgh Steelers.

Three people kayaking in the Allegheny River in front of Heinz Field, home of the Pittsburgh Steelers.

Heinz Field holds over 65,000 people, many of whom arrive five hours before kickoff to tailgate. Closest to the stadium’s  gates, you’ll find the longtime fans who take tailgating to new levels with incredible spreads matched only by their team pride. Blue Lots 7F &7H are where you’ll find the best chefs. Some sell they cook up so bring cash and try a taste of traditional tailgating fare.

Tailgating at the Stage AE Tailgate requires a bit less effort than when you have your own parking spot, but it’s just as fun. This area by Heinz Field is family-friendly, offers indoor & outdoor viewing areas for NFL games, live music and fun tailgate games. If there’s one thing you can be sure of in Pittsburgh, it’s passion from the Steelers’ dedicated fans.

Choose from a variety of FlipKey rentals within walking distance to Heinz Field. This will give you time to get acquainted with the area before game day, and there are many nearby attractions worth visiting. Take the kids to the Children’s Museum of Pittsburgh, visit the Andy Warhol Museum or check out the Market Square Place while you’re in town.

Find a place to stay in Pittsburgh, PA

Kansas City Chiefs | Kansas City, MO

Attending a tailgate for a Kansas City Chiefs game is like going to a massive outdoor party – and one where you’ll likely make a few friends. Arrowhead Stadium is one of the largest NFL stadiums in the country so it’s not surprising that the tailgate scene is renowned. Purchase a single game parking pass in advance and you’ll save money and time on game day by avoiding long lines at the tollgates. Parking lots open five and a half hours before the game for visitors with Early Arrival Tailgate Passes and four hours ahead for everyone else.

Book a vacation rental in downtown Kansas City, and explore the area during your down time. There are several unique museums, such as the Arabia Steamboat Museum and the National World War I Museum and Memorial, that offer interesting exhibits and there’s no shortage of good food here. Be sure to save room for your fix of smoky, saucy Kansas City-style barbecue during your tailgate.

Get ready for the game at a rental in Kansas City, MO

Denver Broncos | Denver, CO

Sports Authority Field at Mile High in Denver, Colorado is a popular spot for tailgating.

Sports Authority Field at Mile High in Denver, Colorado is a popular spot for tailgating.

Don’t be shy at a Denver Broncos tailgate. The city is known for its friendly football fans, making it a fun experience even for out-of-towners. This welcoming atmosphere just might be related to Denver’s standing as the craft beer capital of America, where a cold brew is never far from reach.

Sports Authority Field at mile High has a place for everyone to tailgate no matter the mode of transportation. Fans arriving by car can purchase a parking space for $30 and choose a spot on a first-come, first-served basis. If you don’t have access to a car during your trip to Denver, don’t worry. The Mile High Mountain Village is open to all visitors with a ticket to the game. This area features food and drink specials, flat-screen TVs, appearances from football alumni and cheerleaders and so much more. It’s the perfect option for those that haven’t had time to shop for tailgating supplies.

Even if you don’t have a ticket to the game, you’ll have fun being in Denver on game day. Stay at a rental in the center of the city so you can walk from bar to bar throughout the day. Denver’s vibrant downtown comes alive when the Broncos take the field.

Score a hip rental in downtown Denver, CO

Vacation is stressful! The old adage “I need a vacation from my vacation” was created for a reason. “Who has the boarding passes? Why did Lisa kick her shoes off? Who has the handi wipes? Didn’t we just pass this old Victorian church? Or is this a new one? I swear if we have to wait in another line I’m going to FREAK OUT!”

In honor of World Frustration Day on October 12th we wanted to help ease the tension on your next trip. We understand that going away can be quite a test on your patience and nerves. Whether you’re with your family, as a couple, a group of friends, or even alone – stressors loom around every corner. So we wanted to share a few tactics that can help you relax through the myriad of stressful events that may happen on your trip:

Woman Packing For Vacation Trying To Close Full Suitcase


Lesson 1: Pack lightly. Lesson 2: No, lighter than that. The more luggage you have, the heavier you stuff it, the most stressed out you’ll be when any other of the following situations occur. On your trip you’ll want to dress comfortably, but practically. When do you do pack, aim to bring your most versatile clothes, things that can be worn both actively, but also work as a piece for dressing up. Things you can sit, stand, and walk in for hours on end while still looking fashionable (if you so desire). Rolling your clothes instead of folding will accomplish two things: there will be more space in the suitcase and they won’t wrinkle.

Stuff every nook and cranny of the luggage, you’ll be surprised how many cubic inches you leave unused. Packing a small rolling suitcase will also make your life easier, rather than lugging a duffle bag. Plan ahead by going to a drug store and buying the tiny toiletries you may need on your trip, or the accessories that make travel easier like ear plugs and a sleep mask. And please, go light on the shoes, one or two pairs are sufficient. Spray the luggage with Febreeze to keep the odor fresh and weigh your luggage beforehand to avoid extra baggage fees. Don’t forget a distinct tag for everyone’s suitcase so it is easily recognizable at baggage claim!

delay of the flight

Flight Delay or Cancellation

This is definitely a “make the best of a bad situation” situation. You can never really be sure when a delay will hit you – yes it might be obvious because of snow or rain or cold, but sometimes there’s a mechanical fix or the wing’s need to be iced down or something happened halfway across the world that just somehow affected your trip. If you’re in an airport – head to the nearest restaurant, airline lounge, or bar and enjoy a bit of relaxation time. Did you bring some work with you or a book to read on the plane? Well, start digging in. Make sure you’re seated next to a recharging station, this delay might be awhile.

If you’re really afraid of delays or cancellations, buy flight insurance so you can head home without worry of losing your money. Know your rights when it comes to flights though, and feel free to tweet or Facebook the airline to get status updates and politely game the system. You could also go up to the customer service counter and ask what flights may get you to your destination faster, and they’ll probably rebook you. This may also be a good time to get some sleep to prevent jet lag (see below). You could also make some new friends at the gate, bond over the nuisance.


Woman relaxes in hotel room, asleep on bed

Jet lag

A disruption of your normal sleep schedule and a trip across multiple time zones can often lead to what is known as “jet lag”. There are many tips and tricks to combat this issue so your vacation isn’t ruined by lack of sleep. Taking care of your body is the first step, make sure you’re hydrated and eating healthy before your flight. If you’re on a red-eye, keep going the next day, don’t fall asleep at 9am and sleep through the day, you’ll really mess up your rhythm. Before you leave, start shifting your sleep schedule towards the time zone of where you’re headed – for instance, go to sleep an hour earlier two nights before, and two hours early the night before your trip – that can help you adjust. Avoid alcohol on the plane, your sleeping will be fragmented and you’ll wake groggy instead of refreshed (same with sleeping pills). Try taking melatonin (the hormone that helps you feel tired at night) to adjust your cycle.

Tourists with city map

Getting lost

There are two options to consider when you realize you’re lost in a place you’re not familiar with – enjoy the mystery, or solve the problem. If you don’t mind getting lost, just relax and throw yourself into the adventure of finding your way back. See the nooks and crannies of the city you may have missed by staying in the main tourist areas.

If you want to get back on the beaten path, the easiest step is to ASK someone! If you speak the language, asking how to get back to your vacation rental or restaurant or wherever should be a synch. Another option is to use your smart phone to pull up Google Maps or Apple Maps or whatever app you prefer for directions. Plot a course back to where you need to be. If you’re abroad and do not have an international data plan (though you should highly consider this add-on to your plan if going abroad for a week or more) you should download a map of the city or area when offline before you go. Search for a place in Google Maps and zoom in such that all the area that you wish to save is visible on the screen. Tap the Search button on the keyboard and all the visible area will download to your phone almost instantly.

Waiting in line

The tips for keeping a cool head while waiting in line are endless. The best way to stay calm is wait with a friend! When you’re inside your own head, things can get messy – but if you’re chatting alongside your travel buddy, the time passes faster. The more comfortable your clothes and shoes on, the easier it will be to “do the time” on the line. Make sure your phone is 100% charged before you leave the vacation rental so you can browse for hours if need be, and grab a snack or two to keep yourself fed. If you do have the kids around, try some distracting games like “I spy with my little eye…” or Simon Says. As always, the best tip is to get “there” early so waiting in line becomes less of a necessity. If you’re at a theme park – prioritize which rides you want to go on and try to get those done ASAP, so if there are lines, you know you’ll get on without issues at some point. If allowed, always use the Fast Pass option to cut the long lines. Lastly, bring your favorite book and always know where the closest bathroom is, just in case.

Man picking up wallet

Losing items

Lost items often stay lost, but if you act quickly, you can increase your chances of recovering your item. Don’t panic! Contact the location where you assume you left the item – be it a restaurant, vacation rental, sports stadium – wherever. It may be that a good Samaritan turned it in and it is in the “lost and found” of the establishment. If no luck, and you’re able, retrace your steps and see if you dropped it along the route you came either walking or biking etc. Call the cab company and see if you left it there. If you believe you were robbed, call the police and report the incident immediately. Back up your important documents (like passports) on your mobile device so you can pull them up on your phone in a pinch.

The best strategy though is awareness and prevention. Check for your valuable items always before leaving an area. If possible, don’t even bring valuables with you, so if you lose something, it wasn’t that important anyway.

Crying boy

Unruly children

Traveling with children of all ages is difficult, but young ones especially as they are thrown out of their normal routine into situations that challenge, excite, and confuse them. So the first tip is try to keep as much normal structure and as many rules as possible. If you can keep bedtimes, favorite snacks, toys, and electronics relatively the same, you’re off to a good start. Give the kids plenty of warning that the vacation is upcoming so they aren’t taken unawares, and begin teaching lessons about new situations that might arise, like an ethnic meal that they don’t like. Arrive to all of your events early as kids slow down the boarding/checking in process. Try to keep things simple and streamlined, not much bouncing from activity to activity each day. Schedule time to wind down before bed so kids can fall asleep easier. Watch the food intake on vacation because kids can whine for junk food and candy when on the go! The best way to keep children calm is to keep calm yourself, so keep your cool, if you can.

Typical auto rickshaw taxi tuk-tuk in Khao San Road Bangkok

Taking a taxi in a foreign country

You’re always on high alert when traveling in a taxi or haggling with locals while on vacation. You don’t want to get taken or made to look like a fool. As we mentioned above, it is important to have offline Google maps saved to atleast have a chance to direct the driver where to go. You could also take a physical map with you and try that way – if there’s a language barrier this is especially helpful since you can trace with your finger. In many countries it is still common to charge tourist different prices from locals, and it’s even more common to drive the taxi the long way in order to charge more, so be courteous but be alert!