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October is an ideal month to plan a vacation: fall foliage is at its peak, the weather has found a comfortable midpoint between scorching summer highs and chilly winter lows, and autumn activities abound.

Where To Go In October For Fall Vacations

From the shores of Cape Cod to the mountains of New York, we’ve handpicked 10 fall getaways that are at their peak in October. Each brims with fun—apple picking or wine tasting, anyone?—guaranteeing a great day out at any of our top October vacation spots. Since it’d be impossible to mention all of the classic fall attractions in each city, we’ve highlighted our favorites to check off your fall bucket list.

Make your seasonal stay extra special by booking a vacation rental on FlipKey, and enjoy a comfortable place to relax after a day of merriment. Choose a log cabin and take in the colorful mountain landscape from your private hot tub, or rent a spacious vacation home so your family can spread out at the end of the day. With more than 300,000 rentals to choose from, you’re sure to find just what you’re looking for!

Accord, New York | Westwind Orchard & Cidery

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Located in the shadow of the Catskill Mountains, Westwind Orchard & Cidery is the place to be every weekend from Memorial Day through the end of October. Stroll down the rows of apple trees, filling your sack with handpicked fruit along the way. At the Cidery, sample traditional apple cider, cider with a raspberry twist, and more—all made from the fruits grown on site. And what could be more fall than a mug of sweet apple cider? A freshly baked doughnut dunked in cider!

View all rentals in Accord on FlipKey!

Kansas City, Kansas | Cider Hill Family Orchard

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Cider Hill Family Orchard is just one of the many fall attractions that make Kansas City a top spot for October getaways. Whether you’re in the mood for pumpkin and apple picking, pond fishing, or a relaxing hayride, this family-run orchard has it all. Pack a picnic lunch to enjoy under the shade of one of the big trees out back, or purchase yummy treats like cider doughnuts and kettle corn to enjoy in the comfort of your Kansas City vacation home. Your visit to the Cider Hill Family Orchard will undoubtedly be fun-filled.

View all rentals in Kansas City on FlipKey!

Richmond, Virginia | Richmond Folk Festival

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Mid-October, Richmond floods with folk music enthusiasts from around the country. The city’s eclectic festival features a mix of musicians, dancers, artists, and more, celebrating unique traditions from all over the world. Bounce from stage to stage swaying to the beat of the music, sample a variety of regional, ethnic, and traditional foods, or check out the cultural presentations—there’s no shortage of things to do here.

View all rentals in Richmond on FlipKey!

Guilford, Connecticut | Bishop’s Orchards

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“I will drive an hour to go to Bishop’s,” said one TripAdvisor traveler. We recommend saving yourself the long car ride though, and booking a rental in Guilford for an unforgettable fall getaway. From tasty fruit wine tastings and a gourmet market to the pick-your-own apple orchards and winding corn maze, there’s fun for all ages at Bishop’s Orchards. Here, you get to experience all of the classic fall activities your heart desires right in one place.

View all rentals in Guilford on FlipKey!

Grosse Pointe Park, Michigan | Core Orchards Detroit

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Surround yourself with nature just minutes from downtown Detroit at Core Orchards. It’s the first and only u-pick apple orchard in the area and a source of pride in the community. Designed to increase access to fresh, nutritious foods for those in the neighborhood, the orchard also serves as a welcoming fall attraction. Grab a bag of doughnuts to sweeten your tractor ride out to the farm where you can pluck mouthwatering honey-crisp apples straight from the branches. Once you visit Grosse Pointe Park, you’ll never wonder where to go in October again.

View all rentals near Grosse Pointe Park on FlipKey!

Steamboat Springs, Colorado | Strawberry Park Natural Hot Springs

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Take a break from crisp fall temperatures with a dip in the natural mineral springs at Strawberry Park. Located in Steamboat Springs, these balmy, 104-degree pools are particularly soothing after a day spent hiking through the foliage at Pike’s Peak. Unwind with watsu therapy in one of the private pools or enjoy a massage in the quiet of your own hut. These impressive hot springs are sure to make your autumn escape memorable.

View all rentals in Steamboat Springs on FlipKey!

Plymouth, Michigan | Plymouth Orchards & Cider Mill

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Apples and fall go hand in hand at Plymouth Orchards & Cider Mill in southeast Michigan. With several apple varieties ripe for the picking, award-winning, fresh-pressed cider, and family-friendly wagon rides, it’s the ultimate fall attraction packed into 60 acres of land. The best part though? Admission is free! Plan a trip to Plymouth this season to see for yourself why travelers describe Plymouth Orchards & Cider Mill as a “must visit in the fall!”

View all rentals in Plymouth on FlipKey!

Hampton Falls, New Hampshire | Applecrest Farm

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What’s fall without a weekend getaway in New England? Just 45 minutes north of Boston, the charming coastal town of Hampton Falls is where you’ll find Applecrest Farm, a picture-perfect place to indulge in all things autumn. With pick-your-own-fruit offerings, weekly fall festivals, and a farm-to-table dining experience, it’s no surprise that visitors describe it as a place with “something for everybody!” Plan your trip to this 4th generation gem, and stay just down the road at a spacious rental overlooking the ocean.

View all rentals near Hampton Falls rentals on FlipKey!

Flat Rock, North Carolina | Sky Top Orchard

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Does your ideal fall vacation involve colorful foliage, scenic mountain drives, picking apples and sipping on warm cider? In that case, we know just the place the travel to this October: Flat Rock, North Carolina. This quintessential fall vacation spot is home to Sky Top Orchard, a family favorite with lots of fun and memory-making in store for visitors. Pick a wagon-load of pumpkins, say hello to sheep, goats, chickens, and more in the barnyard, or simply take in the panoramic views. Book a vacation rental in Flat Rock and you’ll have your own u-pick orchard right in your backyard (well, almost!).

View all rentals in Flat Rock on FlipKey!

Wellfleet, Massachusetts | Wellfleet OysterFest

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Are you a foodie wondering where to go in October for a fall getaway? Consider Wellfleet, a quaint fishing town situated at the tip of Cape Cod. While many think of it as a summer destination, the annual Wellfleet OysterFest in October draws visitors to town from all over the region. The event celebrates Wellfleet’s eponymous shellfish grown in the cold, salty waters of Cape Cod Bay. From oyster shucking competitions and cooking demonstrations to spelling bees and live entertainment, there’s something for everyone at Wellfleet OysterFest.

View all Wellfleet rentals on FlipKey!

Best October Vacation Spots

  • Accord, New York
  • Kansas City, Kansas
  • Guilford, Connecticut
  • Grosse Pointe Park, Michigan
  • Steamboat Springs, Colorado
  • Plymouth, Michigan
  • Hampton Falls, New Hampshire
  • Flat Rock, North Carolina
  • Wellfleet, Massachusetts

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Searching for a weekend getaway out West? FlipKey has handpicked 10 top destinations that show their true colors every fall. Whether you’re an adrenaline junkie or a relaxation seeker, you won’t be disappointed. 

Best Fall Weekend Getaways

The arrival of autumn brings cooler weather, colorful foliage… and the urge to get away for a weekend amidst nature. Sip on fine wines in California’s majestic vineyards, marvel at the beauty of the Alaskan wilderness, or enjoy warm weather a little while longer in the Sonoran Desert. No matter your preference, the cities on our list are at their best during the fall.

Now that we’ve narrowed it down for you, all that’s left to do is find the perfect rental on FlipKey. Whether you prefer a cozy retreat tucked away in the woods or an urban oasis just minutes from nature, we’ve got you covered. So what are you waiting for? Call your friends and start planning your unforgettable fall weekend getaways out West this season.

Napa Valley, California

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While there’s no wrong time to visit California Wine Country, Napa Valley is particularly stunning during autumn. The change of seasons brings the grape harvest, and fall color isn’t limited to the trees—gold and russet vines stretch as far as the eye can see. In between wine tastings, tour the vineyards on foot or drift through the air in a hot air balloon. After a fall weekend getaway in Napa Valley, you might just be ready to move here!

See all rentals in Napa Valley on FlipKey!

Portland, Oregon

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Portland is home to picturesque parks, bustling microbreweries and distilleries, and a thriving arts scene that will keep you entertained all weekend long. Stroll along the gallery-lined streets of the Alberta Art District, or spend a leisurely morning browsing at the Portland Saturday Market. Looking to add a splash of color to your photos? Explore the surrounding Willamette Valley mid-autumn when the leaves are at their most vibrant. Whether you choose a modern apartment in the center of the city or an old Victorian home near the river, it won’t be long before Portland feels like home.

See all rentals in Portland on FlipKey!

Anchorage, Alaska

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Score a front row seat to Mother Nature’s breathtaking beauty by renting a cozy cabin in Anchorage. Every autumn, the city glows with the golden hues of leaves and the awe-inspiring aurora borealis illuminates the night sky. Hop on a train to Fairbanks for stunning views of aspen and birch trees, or explore the outskirts of Anchorage on foot. Just keep your camera at the ready—moose are known to cluster at the edges of the city. Another benefit of booking your cabin rental on FlipKey during the fall? You’ll avoid the summer rush in Anchorage.

See all rentals in Anchorage on FlipKey!

Bainbridge Island, Washington

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Just a short ferry-and-bus-ride away from Seattle, Bainbridge Island transforms into a leaf peeper’s paradise every fall. Visitors will be blown away by the blazing red Japanese maple leaves at Bloedel Reserve, a stunning public garden on the island. Prefer an activity the entire family can enjoy? Pick pumpkins off the vine at Suyematsu Farm. If you’re feeling extra ambitious, whip up a homemade pumpkin pie with your day’s pickings in the comfort of your Bainbridge Island rental. We don’t think there’s a better way to cap off the perfect fall weekend getaway out West.

See all rentals in Bainbridge Island on FlipKey!

Aspen, Colorado

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Everyone knows that Aspen is a world-class winter destination. But, it’s also the perfect spot for fall weekend getaways. From hiking scenic trails that meander through Aspen’s iconic Maroon Bells to taking in a bird’s eye view of the foliage from the Silver Queen Gondola, the area is chock-full of fun things to do. Plan your trip here from September through November, and experience the beauty of this destination… before the ski crowds arrive and the bone-chilling winter temperatures set in.

See all rentals in Aspen on FlipKey! 

Coeur D’Alene, Idaho

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Coeur D’Alene should be on everyone’s list of idyllic fall weekend getaways. It boasts a sparkling lakefront location, an all-American atmosphere, and a rugged landscape that attracts outdoor enthusiasts from around the country. Cast your fishing line into Coeur D’Alene’s namesake lake on a crisp fall morning, follow the Tubbs Hill Nature Trail through the wilderness, or go golfing along the water. After a day of adventure, retreat to your rental and enjoy all the comforts of home while on vacation.

See all rentals in Coeur D’Alene on FlipKey!

Bend, Oregon

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Bend has everything fall lovers look for: fiery foliage, an abundance of beautiful nature trails, and mild temperatures. Nestled along the eastern edge of the Cascade Range, it’s the outdoor recreation capital of Oregon and an ideal spot for your fall vacation. Kayaking in the Deschutes River and hiking Pilot Butte are among the best activities during autumn, but there are plenty of craft breweries for those feeling less adventurous. Book a cottage rental just steps from the Deschutes River or stay in an historic home downtown—you’ll find it all in Bend!

See all rentals in Bend on FlipKey!

Flagstaff, Arizona

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Known for its ponderosa pine forests, astounding scenery, and invigorating outdoor activities, a trip to Flagstaff will leave you rejuvenated. The city is set at the base of the San Francisco Peaks, which offer plenty of options for fun in the fresh air. Whether you witness the changing foliage up close on a guided hike or you soar above it on a chairlift ride, there’s plenty to do during a fall weekend getaway in Flagstaff. Book your cabin on FlipKey, and see for yourself why travelers describe this city as a “perfect base-camp to enjoy Northern Arizona.”

See all rentals in Flagstaff on FlipKey!

Palm Springs, California

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For those more interested in chasing summer-like temperatures than seeing colorful foliage, Palm Springs is the place! Located in the desert of Southern California and surrounded by mountains and canyons, this literal hot spot offers ample opportunities for outdoor recreation. Lace up your sneakers for a hike up San Jacinto Mountain, or rent a bicycle to cruise around downtown. Don’t pack your schedule too much though—the refreshing pools and luxurious spas are part of Palm Springs’s appeal.

See all rentals in Palm Springs on FlipKey!

Sun Valley, Idaho

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Sun Valley shines during the fall: warm weather lingers, the crowds are gone, and the leaves begin to change color. Grab your camera and follow the exhilarating trails up Bald Mountain. Don’t settle for halfway up the mountain though—the panoramic views from the top are too phenomenal to miss. In the evening, toast to the day’s adventures at one of the local breweries. Choose Sun Valley for your fall weekend getaway this season, and hit the trails before the snow arrives.

See all rentals in Sun Valley on FlipKey!

Top Fall Vacations Out West

  • Napa Valley, California
  • Portland, Oregon
  • Anchorage, Alaska
  • Bainbridge Island, Washington
  • Aspen, Colorado
  • Coeur D’Alene, Idaho
  • Bend, Oregon
  • Flagstaff, Arizona
  • Palm Springs, California
  • Sun Valley, Idaho

These 10 vacation rentals from FlipKey offer some of the best views of the world’s most notable landmarks—right from your window.

Iconic Vacation Views Right From Your Window

Day dream of waking up to the sunrise over the Eiffel Tower? While sightseeing is on nearly every traveler’s itinerary, there’s no need to limit the best sites in the world to scheduled excursions. From towering skylines and ancient ruins, to modern feats of engineering and otherworldly mountain ranges, FlipKey has rounded up 10 rentals around the world where travelers can take in the most iconic surroundings. All from the comfort of their own living rooms, bedrooms, and balconies.

Vacation rentals provide unparalleled accessibility and ease, putting travelers even closer to the attractions on their list. Whether you’re taking it all in from the window of your private suite or enjoying a night cap on the outdoor terrace, these stunning rentals offer views you need to see (or stay in) to believe.

Roman Colosseum Rental | Rome, Italy

Check out the Roman Colosseum Rental on FlipKey!

2 Bedrooms, 2 Bathrooms, Sleeps 6

History buffs heading to Rome, look no further. This rental is located in the Ancient Rome area, and the private roofdeck terrace offers views of the Colosseum, the Vatican Dome, and the Vittoriano, to name a few.

View all Rome properties from FlipKey!

Piazza San Marco Apartment | Venice, Italy

Check out this Venice apartment on FlipKey!

3 Bedrooms, 4 Bathrooms, Sleeps 6

This spacious, three-bedroom Venice apartment offers stunning views of San Marco and the Campanile bell tower, and 360-degree views of Venice from the private terrace with dining area.

View all Venice properties from FlipKey!

Fantasy Eiffel Duplex | Paris, France

Check out the Fantasy Eiffel Duplex on FlipKey!

4 Bedrooms, 5 Bathrooms, Sleeps 8

Wake up to one of the most iconic views in the world at this luxe 16th arrondissement apartment. The balcony offers stunning Eiffel Tower views, and the central location means easy access to some of the city’s most popular attractions.

View all Paris properties from FlipKey!

Brekka Cottage | Northern Lights, Iceland

Check out the Brekka Cottage on FlipKey!

3 Bedrooms, 1 Bathroom, Sleeps 8

The Northern Lights are one of the most popular bucket list views in the world—and if you’re lucky, you just might spot them from the geothermal tub outside of Brekka Cottage. Regardless of whether you catch the Aurora Borealis, you won’t be disappointed by the views of Sulur Mountain and the Atlantic Ocean from the privacy of the cottage.

View all Reykjavik properties from FlipKey!

Corner Condo | CN Tower, Toronto, Canada

Check out the amazing CN Tower views from this Toronto condo!

2 Bedrooms, 2 Bathrooms, Sleeps 4

Relax in the heart of downtown Toronto in a boutique building with unobstructed views of the CN Tower from a chic 600-square-foot wraparound terrace. The central location offers easy access to nightlife, restaurants, galleries, and shops.

View all Toronto properties from FlipKey!

The Views | Queenstown, New Zealand

Check out The Views rental on FlipKey!

3 Bedrooms, 2 Bathrooms, Sleeps 6

Don’t want to choose between lake, city, or mountain views? Head to The Views in Queensland to soak in all the views from the floor-to-ceiling windows in the open-plan living room and the master bedroom.

View all Queenstown properties from FlipKey!

Matterhorn Alps Apartment | Zermatt, Switzerland

Check out this Swiss Alps apartment with unreal views of Matterhorn!

2 Bedrooms, 2 Bathrooms, Sleeps 5

Make your next ski trip unforgettable by staying in this cozy two-bedroom with views of the Matterhorn. The sunny apartment is walking distance from the ski bus, and includes a jacuzzi bathtub and steam shower so you can unwind after a long day on the mountains.

View all Zermatt properties from FlipKey! 

Tropical Villa | Sugarloaf & Corcovado, Rio de Janeiro

Check out the Tropical Rio Villa on FlipKey!

5 Bedrooms, 7 Bathrooms, Sleeps 10

We doubt you’ll get tired of the ocean views from this infinity edge pool surrounded by lush forest, but if you do, don’t worry. The five-bedroom Tropical Villa also includes a spa with vertical garden and waterfall shower, a home theater, and barbeque area in its luxurious 8,500 square feet.

View all Rio de Janeiro properties from FlipKey!

Liberace Suite | The Acropolis, Athens, Greece

Check out the Liberace Suite on FlipKey!

2 Bedrooms, 2 Bathrooms, Sleeps 4

This opulent suite is located in Plaka, the oldest neighborhood in Athens, at the foot of the Acropolis. After a long day of exploring, travelers looking to continue their cultural experience can relax on the terrace with views of the ancient city.

View all Athens properties from FlipKey!

The Edge | Coral Sea, Port Douglas, Queensland

Check out the amazing Coral Sea views from this award-winning rental!

2 Bedrooms, 3 Bathrooms, Sleeps 5

The only thing that might distract you from these views of Port Douglas is the contemporary architecture of the home itself. With a concrete exterior, sleek balcony with cinematic views of the horizon, and an infinity lap pool, you’re guaranteed a great view no matter where you are in the house.

Check out all Port Douglas properties from FlipKey!


This post was originally published on the TripAdvisor Rentals blog. FlipKey is a TripAdvisor company.

Need to book some one-on-one time? FlipKey has rounded up our top one-bedroom rentals for you and your bae to relax, refresh, and recharge in total privacy and ease.

Romantic Vacation Rentals For You And Bae

From classic romantic getaways like Savannah, Georgia, and Paris, France, to secluded beachside spots in Jamaica, Bali, and the US Virgin Islands—vacation rentals make for the ideal accommodation when planning your next couples getaway. Enjoy stunning features from these top picks like outdoor showers, private pools, dreamy views, breakfast service, and tropical weather. No matter your perfect idea of romance, FlipKey will make your next bae-cation unforgettable at every turn.

Louvre Water Front Designer Apt | Paris, France

Check out the Louvre Water Front Designer Apartment on TripAdvisor!

Bask in the classic Parisian apartment located alongside the river with sweeping views of the Louvre Museum. With ultra-chic French décor, roaring fireplace, baroque fresco ceilings and 24k gold mosaic floors, this cozy, yet decadent property will wow you and your loved one at every turn.

See all FlipKey rentals in Paris!

Tea Treehouse | St. John, US Virgin Islands

Check out the Tea Treehouse on TripAdvisor!

Take romance to new heights in this tropical rental specifically intended for couples. Located on private Coral Bay, this treehouse escape is tucked away along the Caribbean hillside with panoramic sea views, an outdoor shower and spectacular terrace.

See all FlipKey rentals in St. John!

Romantic 1BR | Seminyak, Bali

Check out this romantic 1BR rental on TripAdvisor!

With complimentary daily breakfast, flower petal decorations and romantic décor upon your arrival, this secluded villa has an ultra-private pool, yet is just steps away from Bali’s tropical beaches and famous shopping areas.

See all FlipKey rentals in Bali!

Cottage at Te Moana | Ocho Rios, Jamaica

Check out the Cottage at Te Moana on TripAdvisor!

Located just one mile from the center of town, this tropical rental will feel a world away from everyday life, offering a quiet and dreamy haven designed for two. Soak up the amazing location with an open-air shower, ocean views from the bedroom balcony and quaint touches in this coastal cottage.

See all FlipKey rentals in Ocho Rios!

Luxurious Villa | Reykjavik, Iceland

Check out this luxurious Reykjavik villa on TripAdvisor!

If you and your partner in crime are up for an Icelandic adventure, look no further. This historical house is steps away from the city center, but bursts with charm and privacy. Sit outside and dine al fresco in the back garden, retreat up to your cozy bedroom loft or even take the complimentary car out for a spin.

See all FlipKey rentals in Reykjavik!

Villa Arismari | Crete, Greece

Check out Villa Arismari on TripAdvisor!

Elegance knows no limit in this modern villa. Built in 2017, this retreat is in the picturesque village of Panormo, but has access to a variety of surrounding excursions. If your heart desires a true Grecian experience, look no further and soak in your private pool and world-famous sunsets over the ocean.

See all FlipKey rentals in Crete!

Stylish Modern Villa | Cape Town, South Africa

Check out this stylish Cape Town villa on TripAdvisor!

Enjoy everything Cape Town has to offer from this central apartment in a trendy, walkable neighborhood. Spend the day exploring downtown Cape Town or take a day trip to the exclusive wine estates, and relax in the rooftop hot tub with views of Table Mountain in the evening. For an extra special experience, your host will arrange for a meal prepared in-house by a private chef.

See all FlipKey rentals in Cape Town!

Mirabelle Honeymoon Suite | Savannah, Georgia

Check out the Mirabelle Honeymoon Suite on TripAdvisor!

This romantic one-bedroom apartment is located in the heart of the historic district. The property was originally built in 1900 and faces the St. John’s Cathedral. The building was renovated in 2015 to include luxe furnishings and romantic décor, making it the perfect spot for a romantic Savannah trip.

See all FlipKey rentals in Savannah!


This post was originally published on the TripAdvisor Rentals blog. FlipKey is a TripAdvisor company.

best-coffee-cities

With coffee consumption at an all-time high in the United States, we’ve rounded up 12 of the best coffee cities in the country worth visiting.

America’s Best Coffee Cities

From the historic streets of downtown Boston to the coastal neighborhoods of Santa Cruz, we’ve highlighted 12 of the best coffee cities well-known for their caffeinated brews. Each of these places boasts gourmet coffee shops on almost every corner, making it an impossible task to mention all of them. But we’ve featured our favorite in each city so you can sip more and search less! Whether you’re looking for coffee by the cup or beans by the bag, we think you’ll like these cities a whole latte.

After you decide which destination to visit, opt for a vacation rental from FlipKey to save money during your trip (we know how quickly those specialty coffees can add up!). Enjoy the benefits of extra space and full kitchens—many rentals even have coffeemakers, so you won’t have to leave the house without a cup of coffee to start your day. From modern city apartments to spacious vacation homes, FlipKey offers a variety of rentals to fit every budget and travel style.

Austin, Texas | Caffé Medici

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While you’d think that Austin’s roasting temperatures might curb visitors’ appetite for java, Austin’s coffee scene is booming. And, as new coffee shops are popping up all over town, one continues to stand out: Caffé Medici. Austin’s original specialty coffee shop, Caffé Medici has been perfecting the art of pouring a cup of joe for more than 10 years. From well-balanced, classic coffee to sweet and fruity espresso with a chocolaty finish, the menu here has something to please all palates.

See all Austin rentals on FlipKey!

Boston, Massachusetts | Barrington Coffee Roasting Company

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With long, cold winters and a massive student population, Boston is a city that insists on high levels of coffee consumption. While there are plenty of places throughout the city to fuel up for the day, Barrington Coffee Roasting Company offers some of the best in Boston. It was founded in 1993 out of two friends’ mutual love for everything coffee. Today, the self-described “power-coffee duo” prepares some of the finest coffees from around the world at their Roastery in Lee, MA. The coffee is then delivered fresh to customers and served at their two cafes in downtown Boston.

See all Boston rentals on FlipKey!

Minneapolis, Minnesota | Spyhouse Coffee

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Known for a different kind of brew, too, Minneapolis is happy to share its local coffees all across the country. Case in point: Spyhouse Coffee Roasting Co., which supplies its Orion blend to Caffé Medici on our list. With four cafes throughout Minneapolis, Spyhouse Coffee is a hub for students, professionals, and people of all walks of life. This independent coffeehouse serves an exceptional cup of coffee while educating customers about the sourcing, roasting, and brewing processes, from origin to consumption. Looking for something unique? Try the Spygirl, a latte with lavender and honey.

See all Minneapolis rentals on FlipKey!

Houston, Texas | Siphon Coffee

Located in the Montrose neighborhood, Siphon Coffee has helped put Houston on the map as one of the best coffee cities. This unique coffee shop offers a precise and flavorful cup of coffee using halogen burners and a game-changing siphon brewing method. Working with local Houston roasters, they’ve created a selection of palate-pleasing brewed and espresso based drinks that will satisfy any taste!

See all Houston rentals on FlipKey!

Philadelphia, Pennsylvania | Joe Coffee

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Philadelphia gets coffee fanatics’ stamp of approval—even Ben Franklin’s, a known coffee enthusiast and one of the city’s founding fathers. For some of the city’s finest brews, check out Joe Coffee, a family-owned shop with locations in Philadelphia and New York. The shop has both single-origin and blended offerings on the menu, which they roast in-house. Whether you take your cup on the go or lounge at the cafe, a flawless brew from Joe Coffee will perk you right up.

See all Philadelphia rentals on FlipKey!

Pittsburgh, Pennsylvania | Commonplace Coffee Roasters

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Looking to try the local java in Pittsburgh? Then head to Commonplace Coffee Roasters in Pittsburgh. Since its founding in 2003, multiple locations have opened throughout Steel City, all of which offer a “hug in a mug” with their flavorful brews. Get a boost of energy from a cappuccino or indulge your sweet tooth with a chocolaty mocha. You can’t go wrong, no matter what you order!

See all Pittsburgh rentals on FlipKey!

Portland, Maine | Coffee By Design

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A foodie city in its own right, Portland is also a hub for coffee drinkers with Coffee By Design adding buzz to this coastal destination’s downtown. This combined micro-roastery and coffee bar brews a selection of coffees from exotic grinds, single-origin coffees, and rich roasts. With the smell of freshly brewed coffee wafting in the air, you won’t be able to walk by without stopping in for some liquid joy in a cup.

See all Portland rentals on FlipKey!

Providence, Rhode Island | Bolt Coffee Company

Providence-best-coffee-cities

With sweet “coffee milk” the state drink of Rhode Island, it’s no surprise that Providence makes the cut as one of the best coffee cities in the U.S. Get a quality cup of coffee—hot or iced—at Bolt Coffee Company in the heart of Providence’s historic district. This local purveyor of artisanal coffee expertly pours a precise and intense cup of coffee with each order. From unique carbonated coffees to double shots of espresso, the baristas here take great pride in their product and service, and it shows!

See all Providence rentals on FlipKey!

Santa Cruz, California | Verve Coffee Roasters

Verve-Santa-Cruz-best-coffee-cities

Santa Cruz made our list of the best coffee cities in America because of one-of-a-kind roasters like Verve. Whether you’re starting your day, searching for an afternoon pick-me-up, or need a caffeine fix before tackling the surf, this hot spot has something for everyone. While the shop’s roots remain in Santa Cruz, Verve can be found in cities across the world from Los Angeles to Tokyo. Can’t make it to one of those cities, but want to wake up to Verve coffee aromas every morning? Subscribe and have freshly roasted coffee delivered to your door!

See all Santa Cruz rentals on FlipKey!

Seattle, Washington | Convoy Coffee

best-coffee-cities-america-seattle-washington

What’s a list of the best coffee cities in America without Seattle? Home of the original Starbucks, there are also a multitude of lesser-known local coffee shops throughout the city. One such favorite is Convoy Coffee. For the perfect start to your morning, stop in for an espresso and a Salmonberry Goods pastry. Heading to Seattle for a weekend getaway? You won’t want to miss the weekend Ballard and University District Farmers Markets, where Convoy Coffee sets up a shop with bicycle carts. With its ever-growing rotation of single origin coffees, we recommend visiting often to try them all!

See all Seattle rentals on FlipKey!

Topeka, Kansas | PT’s Coffee Roasting Co.

best-coffee-cities-america

Home of PT’s Coffee Roasting Co.—the standard-bearer for small-batch specialty coffee—Topeka holds its own among the best coffee cities in the country. This local coffee shop’s mission is simple: roast and brew an amazing cup of coffee from the freshest of ingredients. It specializes in serving Direct Trade coffee and espresso, but its diverse menu features options that will satisfy all tastes. From an afternoon meeting over lattes to an evening study break for coffee with Baileys, PT’s Coffee Roasting Co. is a must-visit in Topeka.

See all Topeka rentals on FlipKey!

Washington, DC | Peregrine Espresso

Peregrine-espresso-best-coffee-cities

Washington, DC’s coffee culture continues to expand year after year. The city has more than 1,000 coffee shops and cafes—meaning a jolt of caffeine is never out of reach. One such spot with rave reviews is Peregrine Espresso, a neighborhood cafe that prides itself on offering quality coffee with friendly service. Whether you’re in the mood for a sweet mocha with a dollop of whipped cream or a bold, flash-brewed iced coffee, you can bet Peregrine Espresso has it on the menu. Want to learn about what’s in your cup? The owners—Ryan and Jill Jensen—also love sharing their coffee knowledge with customers through monthly classes about coffee brewing and espresso.

See all Washington, DC rentals on FlipKey!

12 Best Coffee Cities In The U.S. For A Vacation

  • Austin, Texas
  • Boston, Massachusetts
  • Minneapolis, Minnesota
  • Philadelphia, Pennsylvania
  • Pittsburgh, Pennsylvania
  • Portland, Maine
  • Providence, Rhode Island
  • Santa Cruz, California
  • Seattle, Washington
  • Topeka, Kansas
  • Washington, DC

At FlipKey, we value the importance of travel and cultural immersion as a way to learn about the world firsthand, which is why we held a contest to win a $1,000 study abroad scholarship. We asked entrants to tell us in a 1,000-word essay why travel is important to him or her, and we want to send a big thank you to everyone who entered and helped make the contest a success!

A special congratulations to Caroline Brock of Arcadia University in Pennsylvania, the winner of the FlipKey Study Abroad Scholarship! From tuition costs to plane tickets and spontaneous excursions in between, we hope you use the $1,000 to create lots of memories during your semester abroad in Spain.

For those who missed out this year, please submit an essay in the coming year as we’ll be giving away another scholarship in 2018!

The winning essay is printed in full below:

study-abroad-scholarship-winner

Caroline (left) hiking with friends in Snowdonia, Wales.

The first time I left America, I was afraid. I was 16. I had taken six months of Spanish. I was going to be staying with a Spanish family. For just seven days. “Just seven days,” I kept telling myself. “If it’s awful I’ll get through it day by day. Just seven days.” I had packed a box of granola bars in my suitcase in case I couldn’t stomach the food. People have survived on less than a box of granola bars for longer amounts of time than seven days, I told myself. Just seven days. And in ‘just seven days’ I can honestly say that my life changed.

I fell in love with Spain, with the language, the culture, the food, and the people, in just seven days. My suitcase was a pack of granola bars lighter on the flight home—I had tossed those in the nearest trashcan after my first bite of paella. I’m now a Spanish major, and craving the sensation of being in Spain for far longer than seven days. Seven days taught me that taking risks pays off, that no matter what language they speak or food they eat, people are people, and life was made for connecting with as many people as possible. That’s why I chose Spanish as a major, language unlocks so many opportunities to connect with others.

Since that trip to Spain I’d been waiting for the next opportunity to live somewhere new for longer than just a week. I was extremely fortunate to be accepted into Arcadia’s First Year Study Abroad Experience in London. I spent three months in a constant state of awe at the fact that I was doing it, I was living abroad. One weekend, I took a 10-hour bus to Caernarfon, Wales. There I attempted to hike Mount Snowdon, the highest mountain in Wales. When my friends and I arrived at the base of the mountain, we asked a few locals “Which way up?” to which they responded, “Honestly, you’re not really equipped to go up the mountain in this weather,” as they eyed our Sperry rainboots and thing jackets. It was February in Wales, and drizzling. So we went up anyway. We made it about halfway until the rain and wind picked up to the point where we had to turn around. But I can’t describe the feeling of life that I got from that hike. And then the next morning, we got back on the bus to London. We spent about 20 hours on buses that weekend, and about the same amount of waking time in Wales. But those few hours were so full that I wouldn’t trade them for anything. 

Living in London was like living in a dream. Every morning I woke up before class to go on a run through Hyde Park and Kensington Gardens. I couldn’t believe that this life was mine. On some weekends I explore the city, and on others I took a short plane ride to explore a new country. And during the weekdays I was in classes that aimed to engage us in the city—I read Mrs. Dalloway one night and the next I was tracing her steps through the city we both called home. I was reading articles about diversity and seeing it become part of my life as I blissfully battled the crushing crowds around booths from all around the world at Borough Market.

One of the most profound effects that living in London had on me was the self reflection that was imposed on me, both towards myself and my country. People from home were surprised when I told them I would be going abroad half of my first year of college. I just wasn’t the type to take such a large leap of faith. But I proved to myself that I could do it.

And that’s why travel is important to me, because it changes people. After London, I wasn’t the same person as I was before, because visceral experiences like that of living abroad wrench you open and reconfigure you. They make you more confident in yourself, and yet more humble and acknowledging of your position as a small piece to a very, very large world. And I can say that I am still growing, healthily unsatisfied with where I am, with hopes of perpetually tearing my ideas down to form new ones, to change and be changed. Now I’m a mentor for other first year students going abroad to London, and I advise them on how much money they’ll need, remind them to tell their bank they’ll be abroad, make lists of useful tips for the city. But I can’t begin to explain to them the most important aspect of study abroad, they have to experience that for themselves. 

When I go to study abroad in Spain I want every waking hour to be as full as my hours in Wales were. I want to challenge myself, I want to expand my worldview, I want to absorb everything. I want my preconceptions and notions of the world to be shattered and rebuilt into the intricate mosaic that is the human experience on Earth. I want to come back to America and share that with those who haven’t been lucky enough to study abroad. I want to come back and help other people to understand what’s out there. To encourage them to take a risk, to travel, to breathe. Because sometimes in our everyday lives we breathe only because our brain tells us to. I want to fill my lungs with air because I want every cell of my body to experience what my eyes are seeing. I want to breath, and live, with a purpose. 

 Adventure towns for perfect fall vacations.

You don’t have to break the bank to have a once-in-a-lifetime adventure this autumn. With so many canyons, lakes, mountains, and more to explore right here in the US, you’ll find there’s a perfect fall vacation for every budget!

Top Adventure Towns You Can Afford

We looked into the cost of a week-long fall vacation to bring you 12 outdoorsy destinations where adventure knows no bounds. Whether you’re searching for a rock face to scale, a mountain to climb, or a river to cast your fishing line, these adventure vacation spots across the country have it all (and for an affordable price!).

Instead of roughing it in the woods during your trip, consider booking a vacation home with all the comforts and amenities you’re used to. By staying in a FlipKey rental, you can fuel up with a home-cooked meal prepared in your fully-stocked kitchen, or enjoy a comfy bed after a long day outdoors. From secluded mountain retreats to cozy cabins surrounded by trees, all that’s left to do is gather your friends and find the perfect rental in one of these amazing adventure towns.

Prices reflect the median cost for a week-long stay in a two-bedroom rental in that destination, between the months of September, October, and November. 

Pahoa, Hawaii: $795/Week

Discover Pahoa, Hawaii

The alternative to Hawaii’s glitzy, one-size-fits-all beach vacation, Pahoa is a sleepy town known for its abundant natural beauty and laid-back atmosphere. Wade into the waters of Ahalanui Beach Park, a spring-fed pool that’s volcanically heated to a balmy 90 degrees Fahrenheit. For spectacular snorkeling, plunge into the Kapoho Tide Pools. Need a day off from outdoor adventures? Walk along the raised wooden boardwalk, and admire the century-old buildings that give it a “Wild West” feel.

See all Pahoa vacation rentals on FlipKey!

Cody, Wyoming: $959/Week

Cody, Wyoming vacation rentals

Cody, named after its legendary founder, Buffalo Bill Cody, is a charming blend of old and new. It sits at the edge of Yellowstone National Park where buffalo roam (yes, really!), geysers gush, and the pristine wilderness awaits outdoor enthusiasts. Rent a cozy western cabin in Cody and see why travelers describe this one-of-a-kind adventure town as a “must-see!” Filled with natural wonders and a brilliant display of colorful foliage during the fall, choose Cody for your affordable fall getaway.

See all Cody vacation rentals on FlipKey!

McCall, Idaho: $990/Week

River-rafting-McCall-Idaho

This Idaho adventure town may be known for its renowned winter skiing, but plan a trip to McCall during the fall and witness the roadside explosion of color that starts to pop every October. For panoramic mountain views, slip a kayak into the water and paddle around Payette Lake. Prefer to stay on land? Wander through the forests of Ponderosa State Park—which covers a thousand-acre peninsula that juts into the lake, or make a tee time at McCall Golf Club. With its stunning scenery and exhilarating outdoor experiences, you can explore from sun up until sun down in McCall!

See all McCall vacation rentals on FlipKey!

Whitefish, Montana: $1,120/Week

Book a fall vacation in Whitefish, Montana

Once you arrive in Whitefish, however long you’re planning to stay just won’t be enough. Lace up your hiking boots, and head to Glacier National Park, the “Crown of the Continent.” At the park, gaze at the arresting fall foliage or choose a trail—long or short, easy or challenging—for panoramic views of the rugged Rockies. Other activities nearby include cycling, fishing, golfing, and even huckleberry picking. There’s no better time than fall to enjoy all Whitefish has to offer the adventurous vacationer.

See all Whitefish vacation rentals on FlipKey!

Ellijay, Georgia: $1,120/Week

Ellijay-Georgia-fall-vacations

A hidden gem in the Blue Ridge Mountains of Georgia, Ellijay is a quiet town perfect for your fall getaway. Rent tubes and float down the Ellijay River for a unique view of the area, or tour the sprawling local vineyards. And what’s a trip to Ellijay without a stop at the apple orchard? Located in Gilmer County, the “Apple Capital of Georgia,” there are many farms nearby for apple picking. If you’re not feeling active, sit in a rocking chair on your vacation home’s porch and take in the blazing leaves and breathtaking mountain backdrop.

See all Ellijay vacation rentals on FlipKey!

Taos, New Mexico: $1,200/Week

Taos-New-Mexico-river-adventure

Searching for a place that balances thrilling outdoor activities with laid-back, low-key vibes? Then Taos is your answer! Whether you fill your days hiking through Taos Ski Valley (watch out for wildlife!), rafting down the Rio Grande, or marveling at the ancient ruins of Taos Pueblo, there’s never a dull moment here. Rent a private casita on the outskirts of town and escape the hubbub of everyday life.

See all Taos vacation rentals on FlipKey!

Lake Tahoe, California: $1,260/WeekLake-Tahoe-California-adventure-towns

 

What would a list of idyllic fall adventure towns be without Lake Tahoe? Set amidst the jaw-dropping Sierra Nevada Mountains, this city boasts the largest alpine lake in North America and is a hot spot for autumn excursions. Visit the Gondola at Heavenly and ascend the mountains for a bird’s eye view of the area, coast across the clear blue water in a pontoon boat, or hop on a mountain bike to explore. Just one trip to Lake Tahoe will convince you that this destination truly has it all!

See all Lake Tahoe vacation rentals on FlipKey!

Logan, Ohio: $1,266/Week

Logan-Ohio-fall-vacations

Often overlooked, Logan packs lots of adventure within its borders. It’s tucked away in the Hocking Hills region, where you’ll find cascading waterfalls, towering gorges, and dense forest extending for miles—right in Ohio. Need a reward to motivate you along your hike? Make the trek to Ash Cave. This enormous, horseshoe-shaped cave is found at the end a tree-lined path and will take your breath away. Roam the wilderness by day, and cozy up around the fire in your Logan vacation home by night for the ultimate fall vacation.

See all Logan vacation rentals on FlipKey!

Durango, Colorado: $1,330/Week

Adventure towns, Durango, CO

Mountain bikers, hikers, hunters, horseback riders, rafters, fishermen, and more are drawn to Durango. Home to the two-million-acre San Juan National Forest, the roaring Animas River, and an interesting Old West heritage, this outdoorsy destination is one of the top adventure towns to visit, especially during the fall. Tour the scenic landscape on foot, or climb aboard a coal-fired, steam-powered locomotive and travel along the same tracks that early settlers used over a hundred years ago. No matter how you choose to explore, you’ll discover something new in Durango each time you visit.

See all Durango vacation rentals on FlipKey!

Sevierville, Tennessee: $1,374/Week

Adventure-fall-vacations-Sevierville-Tennessee

Picturesque nature trails cut through the colorful foliage, leaves rustle with the wind, and rivers rush down the sides of mountains: Sevierville is at its best during autumn. The city is surrounded by wilderness, with the Great Smoky Mountains National Park only minutes away. At Foxfire Mountain, soar amidst the treetops on a zipline excursion or cross the river by walking the longest swinging bridge in the US, the Bridge to Prosperity. Adventure abounds in the beautiful Smoky Mountains, and you’ll quickly see this hidden gem is no exception.

See all Sevierville rentals on FlipKey!

Moab, Utah: $1,420/Week

Moab-Utah-desert-adventure-towns

Moab’s dramatic landscape and extraordinary attractions beckon all types of outdoor adventurers—hikers, bikers, climbers, white water rafters… you name it! This fiery destination is situated at the edge of Arches National Park and Canyonlands, making it a popular base if you’re looking to explore the extensive network of trails—Balanced Rock and Slickrock—that snake through the sprawling red rock playground. Experience an unforgettable sunrise from 2,000 feet above the Colorado River at Dead Horse Point, or watch the sun dip below the horizon from the backyard of your vacation home.

See all Moab vacation rentals on FlipKey!

Lake Arrowhead, California: $1,551/Week

Lake-Arrowhead-California-Adventure-Town-Vacation

Nestled in the heart of the San Bernardino National Forest and known for its infinite recreational activities, Lake Arrowhead is widely referred to as “The Alps of Southern California.” Its mile-high location provides the ideal setting for hiking, biking, boating, and more. Explore the pine-scented trails that surround this adventure town, drift across the lake in a paddle boat, or browse the specialty shops in Lake Arrowhead Village. With so much to see and do here, you can be sure there’s a new adventure to be had every day of the week!

See all Lake Arrowhead vacation rentals on FlipKey!

Affordable Adventure Towns For Fall Vacations

  • Pahoa, Hawaii
  • Cody, Wyoming
  • McCall, Idaho
  • Whitefish, Montana
  • Ellijay, Georgia
  • Taos, New Mexico
  • Lake Tahoe, California
  • Logan, Ohio
  • Durango, Colorado
  • Sevierville, Tennessee
  • Moab, Utah
  • Lake Arrowhead, California

Top-rated Southern cities for a vacation

With countless places to choose from in the region, we’re highlighting the best Southern vacation spots for renting a summer house. Travelers have spoken, and these destinations have the top-rated review scores for their rental accommodations on FlipKey.

Top-Rated Southern Vacations This Summer

Summer is a fabulous time to visit the South. Warm temperatures linger long into the evenings, allowing plenty of time for exploration, and the region’s cities buzz with activity. Not to mention, the area exudes Southern hospitality, making it a popular place to visit—any time of year.

Whether summer is just beginning or inching to a close, it’s never a bad time to plan that getaway down South! To help you choose your destination, we looked at the average vacation rental review scores for summer stays. The result? Nine of the best vacation spots down South receiving top praise from fellow FlipKey rental guests. From Tennessee to Texas, these Southern vacations (and their top attraction!) come highly recommended by travelers like you.

Consider booking a vacation home for your trip and you’ll be right in the middle of all the action. Not only do rentals provide an affordable home base during your stay, they let you experience the city like a local!

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

9. Decatur, Georgia

Retreat to Decatur, Georgia

Average Vacation Rental Rating: 4.50/5.00

“Lots of heart and soul went into preserving this very special home—if you appreciate craftsmanship and cool old houses, it is worth a visit for that alone!” – FlipKey Traveler

A trip to Decatur reveals what makes this destination so special: beautiful historic homes, a range of unique attractions, and a friendly, small-town atmosphere that is truly one-of-a-kind. At just six miles east of Atlanta, getting to this city—which offers a variety of attractions for foodies, fashionistas, fun-lovers and beyond—is a breeze. Grab a bite to eat on-the-go at Your Dekalb Farmers Market, take a walking tour of the area, or perch yourself on a park bench in Decatur Square. Described as “four square miles of hometown hippiness,” this vibrant city is a hot spot for Southern vacations that can’t be missed.

Our Top Activity Pick: Michael C. Carlos Museum

See all Decatur vacation rentals on FlipKey!

8. Chattanooga, Tennessee

Find your hideaway in Chattanooga, Tennessee.

Average Vacation Rental Rating: 4.56/5.00

“We spent the majority of our time on one of the two decks when we weren’t out hiking. We watched birds fly, the clouds float by, and the hang gliders soar. What a wonderful, relaxing place to enjoy!” – FlipKey Traveler

Nicknamed the Scenic City, Chattanooga lives up to that claim with soaring mountains, extraordinary rock formations, roaring waterfalls, and lots of outdoor activities that let you enjoy it all. Explore the mysterious caverns of Ruby Falls, hike Lookout Mountain for jaw-dropping views, or familiarize yourself with the area on a train ride through the countryside. For an even more memorable stay, rent a cabin amidst towering trees or a private vacation home just steps from the river and make Chattanooga your home, if only for a weekend getaway.

Our Top Activity Pick: Hunter Museum of American Art

See all Chattanooga vacation rentals on FlipKey!

7. New Orleans, Louisiana

Discover New Orleans, Louisiana.

Average Vacation Rental Rating: 4.60/5.00

“Perfect spot in the Marigny!! We could walk easily everywhere we wanted to go and experienced lots of great music and restaurants.” – FlipKey Traveler

Whether your plan is to soak up the local history or dance your way down Bourbon Street, New Orleans is no doubt one of the best vacation spots in the South. It’sa hub of activity from sunrise to sundown. Tour the Garden District—an elegant neighborhood full of Southern charm—where you’ll find pristine gardens and opulent, antebellum mansions. When you’re ready to party, head to Bourbon Street. You’ll find this carnival of sights and sounds in the historic French Quarter. Add to your New Orleans experience by booking a traditional, shotgun-style vacation home just blocks from your favorite attractions.

Our Top Activity Pick: New Orleans Museum of Art

See all New Orleans vacation rentals on FlipKey!

5. Nashville, Tennessee

Nashville, Tennessee

Average Vacation Rental Rating: 4.60/5.00

“Absolutely LOVED this home away from home!! We actually stayed in Friday night instead of going to downtown Nashville just because we loved the house so much!!” – FlipKey Traveler

If you’re looking for world-class music venues, hearty Southern fare, and the chance to spot celebrities both on the stage and in the street, then Nashville is the Southern vacation for you. Take a stroll along the Music City Walk of Fame, check out the Country Music Hall of Fame and Museum, or attend a show at the iconic Grand Ole Opry. At the end of a music-filled day, retreat to the quiet of your beautiful Victorian home rental in Germantown, Nashville’s oldest neighborhood.

Our Top Activity Pick: Adventure Science Center

See all Nashville vacation rentals on FlipKey!

6. Fredericksburg, Texas

Fredericksburg, TX is a hot spot for Southern vacations.

Average Vacation Rental Rating: 4.63/5.00

“This was a great location right in the middle of everything in historic Fredericksburg. A wonderful place to stay with hosts that make you feel like friends.” – FlipKey Traveler

Southern charm will sweep you off your feet in Fredericksburg. It’s located deep in the heart of Texas and is known for its hospitality, rich history, and thriving German traditions. A visit during August lends itself to lazy afternoons watching the grape harvest at a vineyard and warm evenings strolling at the county fair. If you can’t squeeze a trip to Fredericksburg in this summer, don’t fret! With bluebonnets blooming in the spring and Oktoberfest celebrations during the fall, this city is one of the best Southern vacations to take, no matter what time of year it is.

Our Top Activity Pick: National Museum of the Pacific War

See all Fredericksburg vacation rentals on FlipKey!

4. Louisville, Kentucky

Rent a vacation home in Louisville, Kentucky.

Average Vacation Rental Rating: 4.74/5.00

“All the comforts of home. This was much better than a hotel. It was great to have easy access to our events, then drive back into a quiet neighborhood (with deer) in the evenings.” – FlipKey Traveler

With the annual Kentucky Derby spectacle, tasty mint juleps, and a variety of exciting attractions, it’s no surprise that Louisville makes our list of top-rated Southern vacations. Follow the city-wide “Urban Bourbon Trail” to award-winning micro-distilleries, each with its own unique offering of the city’s signature spirit. If you’re a baseball fan, check out the Louisville Slugger Museum, a celebration of the sport’s legends. Choose an historic home within walking distance of downtown, and you’ll never want to leave Louisville!

Our Top Activity Pick: KMAC Museum

See all Louisville vacation rentals on FlipKey!

3. St. Petersburg, Florida

Hit the beach in St. Petersburg, FL.

Average Vacation Rental Rating: 4.84/5.00

“Paradise. This is the first time I ever stayed in a vacation rental—and I think I’ll never go back to hotels again. I felt the most not like a tourist on this vacation compared to others in the past.” – FlipKey Traveler

Known as the “Sunshine City,” St. Petersburg boasts an average of 361 days of sunny skies a year, making it a safe choice if you’re looking to spend your vacation days outdoors. Walk the waterfront for stunning views of Tampa Bay (and even a leaping dolphin or two!) or explore the century-old Sunken Gardens in the midst of this bustling city. One walk along the sugary-sand beaches, one dip in the crystal-clear waters, one stop at the Saturday Morning Market—that’s all it will take to fall in love with St. Petersburg.

Our Top Activity Pick: Great Explorations Children’s Museum

See all St. Petersburg vacation rentals on FlipKey!

2. Hot Springs, Arkansas

Hot Springs, Arkansas Southern Vacations

Average Vacation Rental Rating: 4.85/5.00

“It was the most gorgeous scenic retreat I could’ve asked for. A beautiful hidden gem, just like Arkansas itself!” – FlipKey Traveler

Set among an array of naturally heated springs, Hot Springs bubbles with adventure. From hiking and biking to fishing and kayaking, this Southern city speaks to outdoor enthusiasts. Climb to the top of Hot Springs Mountain to take in the majestic views, discover the beauty of Lake Catherine State Park, or spend a relaxing day at the lake. Book a Hot Springs vacation rental as your base to make exploring even easier during your stay.

Our Top Activity Pick: A Narrow Escape

See all Hot Springs vacation rentals on FlipKey!

1. Greenville, South Carolina

Greenville-South-Carolina-best-Southern-vacations

Average Vacation Rental Rating: 5.00/5.00

“Cozy place, perfect for two. Perfect for peace and quiet and restful relaxation.” – FlipKey Traveler

When it comes to Southern charm, Greenville offers an unforgettable dose. From outdoor concerts to annual street festivals, the city hosts more than 300 events annually, guaranteeing a good time is had by all. Saunter around downtown Greenville—ranked among “America’s Ten Best” by Forbes magazine—taking in the sights and tasting a variety of palate-pleasing cuisines from the more than 600 restaurants in town. This charming destination gets FlipKey travelers’ vote as one of the best vacation spots in the South to rent a summer house. Book a vacation rental here and enjoy all the city has to offer with the picturesque Blue Ridge Mountains as your backdrop.

Our Top Activity Pick: Roper Mountain Science Center

See all Greenville vacation rentals on FlipKey!

9 Best Southern Vacations

  • Decatur, Georgia
  • Chattanooga, Tennessee
  • New Orleans, Louisiana
  • Fredericksburg, Texas
  • Nashville, Tennessee
  • Louisville, Kentucky
  • St. Petersburg, Florida
  • Hot Springs, Arkansas
  • Greenville, South Carolina

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

Looking for a way to cool off on your next vacation? Then you’re in luck, as FlipKey has pulled together a round-up of the 10 most insane private pools around the world. Travelers will fall in love with these jaw-dropping rental homes.

From a stunning infinity pool in Mykonos to a Malibu, California edge pool with unparalleled views, FlipKey wants you to dive head-first into relaxation and luxury.

All properties below are available to rent from FlipKey, where travelers can search, compare, and book hundreds of thousands of properties worldwide, including cabins, beach houses, desert hideaways, and more. Plus, feel confident in your decision with our Payment Protection.

Nafiska Estate | Santorini, Greece

5 Bedrooms, 5 Bathrooms, Sleeps 10

Check out Nafiska Estate on FlipKey!

Land in the private helipad and dive in the estate’s unrivaled pool overlooking Santorini’s famous volcano and sprawling ocean views. With simple yet clean interior design, this secluded Santorini spot will exceed every expectation.

See all Santorini rentals from FlipKey!

Royal Hawaiian Estate | Oahu, Hawaii

6 Bedrooms, 5 Bathrooms, Sleeps 12

Check out the Royal Hawaiian Estate on FlipKey!

Enjoy island life like never before. With an open floor plan and expansive floor-to-ceiling windows, guests soak in oceanfront views of Waimanalo Beach from every angle. Outside, spaces offer flexibility for entertaining including an outdoor bar, barbecue area, terrace, and inviting pool with a built-in slide and lava rock waterfall.

See all Oahu rentals from FlipKey!

Camin Villa | Crete, Greece

4 Bedrooms, 3 Bathrooms, Sleeps 8

Check out Camin Villa on FlipKey!

Blending the amazing view with exquisite architectural design, this rental offers pure relaxation in the embrace of the Cretan nature. The property boasts a rare infinity pool that flows through the home’s interior and can even be accessed via bedroom quarters. The overlooking deck pairs perfectly to offer spectacular views of sea, olive groves and mountains.

See all Crete rentals from FlipKey!

Endless Views Estate | Malibu, California

6 Bedrooms, 7 Bathrooms, Sleeps 13

Check out Endless Views Estate on FlipKey!

This beachfront luxury property is situated on the golden sands of Broad Beach in Malibu. Designed and furnished by the renowned architect, Waldo Fernandez, this breathtaking villa boasts near-endless views of the Pacific, and is the epitome of beachfront living with every ounce of comfort and class awaiting you.

See all Malibu rentals from FlipKey!

Villa Degli Affreschi | Amalfi Coast, Italy

8 Bedrooms, 9 Bathrooms, Sleeps 15

Check out Villa Degli Affreschi on FlipKey!

Built in 1741, Villa degli Affreschi features a lush garden surrounding the property, a pool overlooking Positano and ten lavish bedrooms—plus an in-house chef and a complimentary cooking lesson. Spend a lazy morning in bed before opening the doors to your private terrace for a taste of the salty sea breeze.

See all Amalfi Coast rentals from FlipKey!

Villa Superview Chrysantina | Mykonos, Greece

4 Bedrooms, 6 Bathrooms, Sleeps 8

Check out Villa Superview Chrysantina on FlipKey!

While still a traditional Myconian house, this villa offers a magnificent view of Delos, Rinia and Syros islands, giving travelers a stunning once-in-a-lifetime sunset experience. Situated on the ideal vantage point, travelers can soak in the natural beauty poolside with unparalleled 360-degree views of the island.

See all Mykonos rentals from FlipKey!

Villa Sunyata | Phuket, Thailand

8 Bedrooms, 8 Bathrooms, Sleeps 16

Check out Villa Sunyata on FlipKey!

With tranquil sunsets over the Andaman Sea, travelers will swim to their heart’s content in a sleek infinity pool while enjoying direct access to a private cove. Just a five-minute walk from the heart of the vibrant Kata Beach and boasting the most attentive staff, this home truly leaves guests feeling pampered.

See all Phuket rentals from FlipKey!

Villa Pippa | Seminyak, Bali

3 Bedrooms, 3 Bathrooms, Sleeps 6

Check out Villa Pippa on FlipKey!

Located steps away from some of the best hotspots in Bali, this villa offers modern style mixed with Bali charm. The private swimming pool is surrounded by a garden oasis teeming with greenery and sliding glass doors can be fully opened, so guests can readily access the outdoor living space.

See all Bali rentals from FlipKey!

Malibu House | Malibu, California

4 Bedrooms, 4 Bathrooms, Sleeps 10

Check out the Malibu House on FlipKey!

This sprawling private retreat has luxury engrained in every detail. From an 18th century fountain, chateau look, antique hand plastered walls, imported French fireplaces, and a hidden theater room, this grand residence also features an expansive outdoor space with a 200 bush rose garden and fresh water pool.

See all Malibu rentals from FlipKey!

Finca Miquelet | Majorca, Spain

5 Bedrooms, 5 Bathrooms, Sleeps 10

Check out the Finca Miquelet on FlipKey!

Bask in the beauty of the Balearic Islands. With charming Majorcan accents, this sophisticated hideaway offers an idyllic pool terrace with magnificent landscape and coastline views. With splashes of blue and detailed tiling, the interior rivals the scenic outdoor surroundings.

See all Majorca rentals from FlipKey!


This post was originally published on the TripAdvisor Rentals blog. TripAdvisor is the parent company of FlipKey.