Places to Stay

Our Favorite Vacation Homes in America’s Most Beautiful Small Towns

Charming decor, fantastic views, and reading nooks galore.

October 25, 2023

best small towns in america Whitefish Montana

In a world where travel often revolves around major cities, small towns can feel like well-kept secrets. But there are many advantages to setting aside some vacation days for places more off the beaten path—and we’re not just talking about the relative lack of crowds. The best small towns in America are ideal for both relaxation and adventure, with picture-perfect downtown neighborhoods sitting adjacent to some of the country’s most magnificent landscapes.

And while small towns are known for their cute inns and B&Bs, these accommodations can be tiny, and—depending on the season—the rooms may get snatched up fast. That’s where rental companies like Airbnb and Vrbo come in. These platforms have homes available in almost every US town you can think of (or at least options close by), and some of them are cuter than any boutique hotel you’ll ever find.

Need proof? We revisited our list of the most beautiful small towns in America, and searched for the best vacation rental in each of the 28 featured destinations. Our findings—a delightful medley of log cabins, tiny cottages, and beautiful mountain chalets—are gathered below.

As a bonus, all of these selections are run by Superhosts, who each have a rating of 4.8 or above, a record of zero cancellations, and at least a 90 percent response rate, meaning that even though they get tons of requests, they'll get back to you ASAP.

While we have not stayed in every rental featured, unless otherwise stated, these listings are vetted based on Superhost status, amenities, location, previous guest reviews, and decor. This gallery has been updated with new information since its original publish date.

All products and listings featured on Condé Nast Traveler are independently selected by our editors. If you purchase something through our links, we may earn an affiliate commission.

Avalon, California
Avalon is all about the water, so properties overlooking the coast are obviously prime real estate. This oceanfront villa delivers on all fronts, with walls of windows and a covered balcony affording unobstructed views of the harbor. The one-bedroom rental is perfect for a couple’s retreat or solo trip, and the Spanish-style architecture and decor will make you feel like you’ve jetted off to Europe rather than California.
$382 at Airbnb (Starting Price)
Bar Harbor, Maine
Right in the heart of downtown Bar Harbor, this is certainly one of the most unique accommodations in the entire town. The building served as a convent in the early 1900s, and you can still see remnants of the house’s holy past: think stained glass windows, arched wooden doors, towering beam ceilings, and even the original private entrance to the chapel’s confessional. If you do decide to book this listing, you should also go ahead and invite your entire extended family—the biblical biggie has eight bedrooms and sleeps up to 16 people.
$800 at Airbnb (Starting Price)

Block Island, Rhode Island
Block Island is a New England getaway at its best, complete with lighthouses and seagrass-lined beaches. While the small downtown area is a great place to stock up on antiques, you’ll want to spend most of your time near the water—so a beach house is your best bet. This cedar-shingled, three-bedroom house sits above a private rocky beach, which you can see from nearly every angle in the living room. The upper-level bedroom suite provides similar views. On rainy days, take a soak in the clawfoot tub or grab a book and curl up in one of the many plush armchairs.
$500 at Vrbo (Starting Price)
Cannon Beach, Oregon
It’s hard to imagine a better rental in Cannon Beach than this three-bedroom house, which showcases the Oregon coast perfectly with direct beach access, windows, and a deck overlooking the Pacific Ocean, and even views of the famous Haystack Rock from the living room. As an added bonus, the light wood-paneled interiors and gray-shuttered facade look like they were pulled from Nancy Meyers’s personal vision board.
$287 at Airbnb (Starting Price)

Cape May, New Jersey
There’s a lot to love about Cape May, whether you prefer the Victorian charm of the downtown area or the beachy vibes closer to the shore. We chose a rental that embraces the latter—a recently renovated beach house with four bedrooms and two spacious decks overlooking the water. It’s only a five-second walk from the back deck to the ocean, and you might even spot some humpback whales if you time your visit right (viewing season runs from March to December, though June to September are the true peak months).
$825 at Vrbo (Starting Price)
Carmel-by-the-Sea, California
If you combined the two houses from The Holiday—Kate Winslet’s Surrey cottage and Cameron Diaz’s Los Angeles mansion—it might look something like this charming Carmel-by-the-Sea rental. When you’re craving a cottage experience, you can sip tea in the two-bedroom's manicured gardens or read a book on the window seat. Then when you’re ready for some high-tech luxury, the large-screen Roku TVs and fully loaded kitchen are there waiting for you. (Jude Law, however, is not included.)
$1,072 at Airbnb (Starting Price)

Deadwood, South Dakota
While the town of Deadwood gives off major Old West vibes, there’s no need to forego any modern comforts during your visit—especially if you stay at this incredibly stylish three-story cabin. Located in the Black Hills outside of town, this rental is a quiet and cozy retreat with an A-frame roof, massive windows, a stone fireplace, and a hot tub in the backyard.
$433 at Airbnb (Starting Price)
Eureka Springs, Arkansas
Eureka Springs is a tiny town tucked away in the Ozark Mountains—one of the Midwest's most beautiful natural assets—that shines with its juxtaposition of crystal shops, quirky galleries, and haunted hotels. This cabin takes full advantage of its surroundings, located right on the edge of the main downtown area but still removed enough to enjoy some peaceful quiet (you’ll love the firepit in the private backyard). The one-bedroom home’s interior is bright and colorful, with stained-glass windows and pops of red decor.
$187 at Airbnb (Starting Price)

Friday Harbor, Washington
Surrounded by trees and overlooking Griffin Bay, this gated estate is a great spot for a fun-filled yet relaxing family vacation. It features four bedrooms and spacious common areas, plus expansive grounds that include a hot tub and badminton court. And the house is only three miles from Friday Harbor, where you can visit the farmers market and great restaurants.
$381 at Airbnb (Starting Price)
Harpers Ferry, West Virginia
Harpers Ferry is steeped in history and surrounded by magnificent nature, and most rentals here are as traditional as the town itself. That only makes this eclectic two-bedroom Airbnb stand out even more, with its colorful walls and mix of vintage and modern decor (a neon sign hangs over the living room’s antique rug, for example). The back patio is a lovely space to spend a cool evening, and the house’s proximity to downtown Harpers Ferry just seals the deal.
$166 at Airbnb (Starting Price)

Jekyll Island, Georgia
Jekyll Island is probably most famous for its historic Jekyll Island Club Resort, but visitors have plenty of rental options to choose from as well. Just check out this spacious townhouse, complete with four bedrooms, a charming front porch, and a community pool. Guests can even walk to the beach via a boardwalk winding through the forest.
$445 at Airbnb (Starting Price)
Ketchikan, Alaska
If you really want to get away from it all (which you probably do, if you’re traveling to Alaska), you can’t do much better than this oceanfront cabin. The three-bedroom home is all about connecting with nature—time your visit right, and you might even get to see breaching whales and bald eagles without even having to leave your porch.
$195 at Airbnb (Starting Price)

Lake Placid, New York
If you visit the Adirondacks and don’t stay in a log cabin, did you really even visit? This five-bedroom cabin (which is really more of a chalet) has it all: cushy furniture, sheepskin rugs, a stone fireplace, a large back deck with Adirondack chairs (duh), and evergreens as far as the eye can see. It’s also located just a 15-minute drive away from Whiteface Mountain.
$850 at Airbnb (Starting Price)
Leavenworth, Washington
The town of Leavenworth was modeled after the villages of Bavaria, Germany—fitting, then, that this two-bedroom home looks like something you might find in a Grimm fairytale. Every detail of the log cabin raises the coziness factor, including vaulted wood ceilings, stone fireplaces, handmade velvet curtains, and a clawfoot tub. Enjoy a hot toddy at the outdoor fire pit or covered front porch; if the weather is too cold, bring the fun indoors and watch a movie on the big screen.
$344 at Airbnb (Starting Price)

Magnolia Springs, Alabama
Magnolia Springs is the epitome of Southern charm, from its oak tree-lined streets to its old churches. This studio apartment is located in Fairhope (about a 25-minute drive from Magnolia Springs), but features all the same appeal. The vaulted ceilings and furniture made from reclaimed materials are full of personality, while the private back porch is the perfect place to finally catch up on that book you’ve been meaning to read.
$160 at Airbnb (Starting Price)
Marfa, Texas
This 90-year-old, two-bedroom adobe home is a mashup of artsy culture and pure Texas charisma—much like the town of Marfa itself. Take some time to appreciate the custom artwork and photography on the walls, then head outside to take a nap in one of the hammocks or sip drinks around the fire pit. The host also suggests you “start your day slow while listening to Dolly on vinyl,” which sounds pretty darn good to us.
$161 at Airbnb (Starting Price)

Nantucket, Massachusetts
This four-bedroom house—affectionately named “Sweet Pea”—has all the makings of an ideal Nantucket getaway: rustic shiplap walls, preppy prints on pillows and ottomans, wicker bedroom furniture, and even an outdoor shower to rinse off after a day at the beach. The entire home (about a 15-minute walk to downtown) was renovated in August 2021, and you can expect brand-new bedding and light fixtures tucked between the owner’s collections of antiques.
$579 at Airbnb (Starting Price)
Paia, Hawaii
Located on Maui’s North Coast, the town of Paia is all about the beach—so don't even bother looking for an inland rental. This four-bedroom house is about a minute’s walk from the shore, and you can see the ocean from almost every room (the A-frame windows in the third bedroom are a major selling point). When you're not actually on the beach looking for sea turtles, enjoy the scenery from the deck or ground-level lanai.
$850 at Airbnb (Starting Price)

Portsmouth, New Hampshire
Portsmouth is a quintessentially charming New England town, complete with a downtown area that puts Stars Hollow to shame. This artsy loft is located smack dab in the middle of Market Street—one of downtown Portsmouth’s main stretches—and even has a string light–lined balcony facing the storefronts. The interior is equally cute: think exposed brick, funky wallpaper, and tons of artwork.
$239 at Airbnb (Starting Price)
Sedona, Arizona
If you can’t find a reasonable rate at one of Sedona’s luxury resorts, this studio is a viable substitute. The upper-level studio has all the necessities—brick fireplace, memory foam mattresses, views of the red rocks—but a stay here goes far beyond sleeping quarters. Guests will also have access to the property’s saltwater pool, dry sauna, hot tub, and aromatherapy steam room, and can even add on a deep-tissue massage, reiki session, or wine tasting class for an extra fee. Note: Be sure to book this listing well ahead of your desired travel dates, as it tends to fill up five to six months in advance.
$573 at Airbnb (Starting Price)

Snowmass Village, Colorado
While nothing compares to Colorado’s mountains when it comes to sheer beauty, this chalet outside of downtown Snowmass is a close runner-up. The four-bedroom house was designed to keep guests close to nature at all times, with tall rooms bathed in natural light and tons of windows offering glimpses into the surrounding aspen groves. There’s even a sizable back deck for enjoying al fresco meals on warmer days.
$998 at Airbnb (Starting Price)
St. Augustine, Florida
When you visit St. Augustine, you probably are expecting ocean views and gorgeous Spanish architecture—and this two-bedroom house just so happens to provide both. The 1930s home features red roof tiles outside and vaulted ceilings inside, while the rooftop deck (covered with string lights, of course) provides unparalleled views of the marshlands and Atlantic Ocean. There’s also a hot tub where you can watch the sunset with a glass of Rioja in hand.
$375 at Airbnb (Starting Price)

St. Michaels, Maryland
Located on the water just outside of historic St. Michaels, this five-bedroom house is spacious, bright, and filled with gorgeous antique furniture. It’s hard to find an inch of wall space that isn’t occupied by windows, so you can sit back and enjoy Chesapeake Bay views from almost every room (the floor-to-ceiling windows in the primary suite are particularly fabulous). Be sure to spend at least a couple of afternoons in downtown St. Michaels, although we understand if you can’t pull yourself away from your temporary home.
$757 at Vrbo (Starting Price)
Stowe, Vermont
Stowe is an absurdly quaint town, and many of its buildings and churches date back to the 1800s. This three-bedroom house may not be as historic as its surroundings, but it certainly is just as pretty. The pièce de résistance of the home is the A-frame living room, adorned with potted plants and encased by walls of windows and skylights—you don’t want to miss a single second of gently falling snow (or fall foliage), after all.
$457 at Airbnb (Starting Price)

Taos, New Mexico
Taos is known for its thriving arts community, so you’ll want an Airbnb that reflects its creative surroundings. This boho adobe more than fits the bill, complete with indoor hammocks, repurposed wood beams, and decor that includes cow skulls and terracotta tiles. Fun fact: The house used to be the studio of a prominent flamenco dancer. How’s that for artsy?
$131 at Airbnb (Starting Price)
Whitefish, Montana
Whitefish was one of Airbnb’s top trending destinations in 2021, so you better believe there are tons of great rental options here. Case in point: this absolutely stunning ski chalet, which is basically the structural personification of hygge. From the hanging wood fireplace to the A-frame living room with walls of windows, this entire three-bedroom home is a luxurious slice of Scandinavia in northwest Montana.
$821 at Airbnb (Starting Price)

Caitlin Morton has been writing about travel for nearly a decade, with bylines in Vogue, Travel + Leisure, AFAR, TripSavvy, Real Simple, and more. She enjoys baked goods, Ireland, orange nail polish, and horror movies. One time she held the door open for Ian McKellen, which is as close to... Read more

TopicsAirbnbs

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