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Leaf Peeping Trips: 15 Best Fall Vacations In Small Town, USA

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It can be sad to say goodbye to summer. But dry your eyes, because we know you’re secretly excited about what the next season has in store. A kaleidoscope of natural color. Cool, crisp air that marks a fresh beginning. And all the plaid and wool you’ve been dying to fish out of the closet. Admit it. Fall’s fantastic.

Best Fall Vacations For Small-Town Color

Rugged peaks, glistening lakes, tumbling falls, and woodland hideaways that make the daily grind seem a million miles away. That’s what we look for in the ultimate fall vacation. Tiny mountain towns don’t generally provide a lot of hotel accommodation, so a rental is often the best option. And what avid leaf peeper wouldn’t want to stay in a cozy log cabin in the woods, anyway?

We’ve rounded up some of the best fall vacations this season in America’s most charming small towns, each offering a range of vacation rentals to book from FlipKey. Choose a spacious home for friends and family, or an intimate retreat for a couples getaway. You’ll enjoy a fully stocked kitchen and peaceful surroundings that’ll have you destressed and refreshed in no time—not to mention an incredible display of fall foliage right out your window.

Now layer up, grab a hot drink, and read about these 15 best fall vacations in Small Town, USA.

Sugar Hill, New Hampshire

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“The cabin was immaculate, with plenty of space for the whole family. The view from the balcony is truly breathtaking—we got some awesome pictures of the moon between the trees! ” — FlipKey Reviewer

Sugar Hill is one of the best fall vacations in New England: a teeny tiny town with front-row views of the White Mountain National Forest. It’s small, it’s off the beaten path, and its fall foliage really is a sight to be seen. Quaint Sugar Hill offers one of the most picture-perfect backdrops for ushering in the new season.

See all FlipKey rentals in the Sugar Hill/White Mountain area!

Dawsonville, Georgia

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Dawsonville is situated right by the magnificent Amicalola Falls State Park, a terrific leaf peeping spot known for its thundering 729-foot waterfall. This is also great birdwatching territory and you’ve got the Etowa and Amicalola Rivers to paddle about in. While you’re here, you might as well try a tour and a tasting at the Dawsonville Moonshine Distillery, too.

See all FlipKey rentals near Dawsonville!

Estes Park, Colorado

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“This cabin was absolutely charming and everything we were hoping for in a mountain retreat. The location was spectacular, yet easy to get into town or up to the park.” — FlipKey Reviewer

Estes Park is a great place for a cabin vacation, and one of the best fall vacations out West. It’s a traveler-preferred starting point for exploring the stunning Rocky Mountain National Park. Tackle early-morning hikes to get breathtaking sunsets over rocky peaks as your reward. Breathe in the crisp mountain air, watching bighorn sheep and elks roam free, and see the golden leaves do their thing as far as the eyes can see.

See all FlipKey rentals in Estes Park!

Blowing Rock & Banner Elk, North Carolina

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Blowing Rock is known as the ‘Crown of the Blue Ridge’, and attracts hikers, skiers, spelunkers, and spa fans alike. It has cozy cabins galore with views to die for. If you’re planning a fall vacation to this area, there’s also nearby Banner Elk, where the splendid reds and golds are vivid enough to render spectators speechless.

See all FlipKey rentals in the Blowing Rock/Banner Elk area!

June Lake, California

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This is a small, friendly community in the eastern Sierra Nevada region, where you can enjoy the peace of sparkling June Lake and its smaller neighbor, Gull Lake. People come here for the excellent watersports facilities, the hiking trails, the inspiring mountain views—and, of course, the spectacular fall colors. June Lake might be the best fall vacation you don’t know about.

See all FlipKey rentals near June Lake!

Hunter, New York

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You can see why New Yorkers love having Hunter within easy reach. This charming mountain resort in the Northern Catskills has plenty of small-town appeal, and draws cyclists and zip-lining fans to enjoy the scenery in its autumnal glory. A tour on the Scenic Skyride Chairlift provides thrills and unforgettable views of the fall foliage.

See all FlipKey rentals in Hunter!

East Stroudsburg, Pennsylvania

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East Stroudsburg has some historic buildings and a thriving arts and crafts scene, providing plenty of mementoes to take home. It’s also a handy base for viewing the forested peaks of the Pocono Mountains, walking the rugged hiking trails of Worthington State Forest, and watching the rushing waters of Bushkill Falls, also known as the “Niagara of Pennsylvania.” To see the beautiful colors from above, opt for a thrilling skydive…if you dare.

See all FlipKey rentals in East Stroudsburg!

Pigeon Forge, Tennessee

Pigeon Forge, Tennessee

“Breathtaking sights, beautiful cabin, relaxation to the fullest. Our first time to stay in the mountains. Amazing views! The cabin was awesome with everything you needed to set up house!” — FlipKey Reviewer

Strap on your hiking boots and don your woolen hat. You’re going leaf-crunching in the Great Smoky Mountains. Driving tours are particularly recommended here and there are some excellent routes for taking in the seasonal colors and the odd glimpse of the local wildlife. Hmm, but what else makes Pigeon Forge one of the best fall vacations? Dollywood, of course! It just wouldn’t be right to come here without visiting the theme park masterminded by the country-singing icon who grew up in a tiny cabin in nearby Locust Ridge.

See all FlipKey rentals in Pigeon Forge!

Luray, Virginia

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Luray sits in the Shenandoah Valley between the Blue Ridge Mountains and the Massanutten Mountains. The best way to appreciate the fall foliage here is to take the Skyline Drive, a 105-mile stretch of road through this scenic area. You can also tour the famous Luray Caverns, which shelter a jaw-dropping array of huge rock formations.

See all FlipKey rentals in Luray!

Hendersonville, North Carolina

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“So quiet and secluded, which is what we love. Made s’mores out in the fire pit, barbecued on the grill, and ate outside on the deck, felt like we were in a tree house.” — FlipKey Reviewer

Hospitable Hendersonville is another picturesque mountain town where people can leave the rest of the world behind. It’s not far from here to Dupont State Recreational Forest, where you can follow scenic trails and see tumbling waterfalls. This stunning natural landscape is so beautiful and vast it was chosen as a backdrop for The Last of the Mohicans and the 2012 Hunger Games movie.

See all FlipKey rentals in Hendersonville!

Lake Almanor Area, California

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The Lake Almanor reservoir in Plumas County is a peaceful spot, perfect for those who want to be by the water to fish, hike, and sail. Enjoy serene forest walks or explore the welcoming little towns dotted around the lake’s shore, where there’s always something fun going on.

See all FlipKey rentals near Lake Almanor!

Blue Ridge, Georgia

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The mountain town of Blue Ridge is rich in cozy hideaways offering gorgeous vistas. You’ll love the relaxed pace of this gentle town, where you can ride the Blue Ridge Scenic Railway, try a bit of trout fishing, or shop for antiques and artworks to take home.

See all FlipKey rentals in Blue Ridge!

Cleveland, South Carolina

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“Perfect retreat for a cozy getaway… This cabin was the perfect getaway where we could turn down the noise of the city and listen to the peaceful sounds of country life. The cabin is beautifully and thoughtfully built with every amenity.” — FlipKey Reviewer

Maybe not your first guess of the best fall vacations in America, but Cleveland is a great base for some truly breathtaking fall scenery. Follow the steep road to the top of Caesars Head State Park for the best views of the changing colors and the majestic Blue Ridge Mountains. There are some excellent hiking trails around here too, some of them pretty challenging, so do your research before you set off.

See all FlipKey rentals near Cleveland!

Stowe, Vermont

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Who likes their leaf peeping with a side of adrenaline? If you’re in Stowe, sign up for a Ziptour Adventure and see the local fall foliage from above, whizzing high above all the reds, browns, and golds. If you prefer to keep your feet firmly on the ground, try the hiking trails and take in that mountain scenery in a more sedate fashion. While Stowe is renowned for its winter skiing, this Green Mountain State gem is also one of the best fall vacations you can take.

See all FlipKey rentals in Stowe!

Mystic, Connecticut

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Some say Connecticut looks its most beautiful in the fall. There’s no better place to find out for yourself than this little destination on the banks of the Mystic River. Explore the town with Mystic Bike Rentals, take to the trees (in a safety harness) at the Fields of Fire Adventure Park, go walking at Haley Farm State Park, and see all colors of fall at Pequot Woods.

See all FlipKey rentals in Mystic!