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There are many advantages to vacationing in small towns, from friendly locals to surprisingly great food. You’ll also often stumble upon some of the cutest inns and B&Bs you’ll ever see. The only downside? These places can be tiny, and, depending on the season, they fill up fast.
That’s where rental companies like Airbnb and Vrbo come in. They have homes available in almost every U.S. 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 26 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.
All products featured on Condé Nast Traveler are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.
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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.
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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.
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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.
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Telluride, Colorado
While nothing compares to the Rocky Mountains when it comes to sheer beauty, this architectural masterpiece outside of downtown Telluride is a close runner-up. The three-bedroom house was specifically designed to bring the outside in, with 20-foot windows, wood floors and ceilings, and nature-inspired murals and photographs. Enjoy the views of the mountains and aspen groves from the lower-level patios or, better yet, the hot tub.
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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.)
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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.
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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.
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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.
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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.
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Sitka, Alaska
If you really want to get away from it all (which you probably do, if you’ve traveled to Sitka), you can’t do much better than this Japanese-inspired house. The open-concept home was designed to immerse guests in nature, as evidenced by the floor-to-ceiling windows and wraparound deck with sliding glass doors. The three bedrooms are well-lit and peaceful, and there’s even a tea room with traditional Japanese tatami mats.
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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 afternoons in downtown St. Michaels, although we understand if you can’t pull yourself away from your temporary home.
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Montpelier, Vermont
Whether you visit in the fall for leaf peeping or in the winter for skiing, this two-bedroom Vermont chalet—about a 20-minute drive from downtown Montpelier—provides the perfect refuge. The mountain-facing living room has a wall of windows that leads to the sprawling back deck, allowing guests to fully enjoy the gorgeous surroundings (there’s even an outdoor shower if you really can’t pull yourself away from the views). The fireplace and sheepskin rugs provide tons of coziness, and nearly every room has a comfy reading nook.
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Camden, Maine
This Camden property is already booked up through the end of June, and honestly? We’re not surprised. The light-filled, three-bedroom home is not only impeccably designed, but it offers both peaceful seclusion and quick access to downtown Camden. The huge collection of books, colorful artwork, and potted plants in every room make this an absolutely lovely place to spend a few nights.
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Saugatuck, Michigan
Why stay near Lake Michigan when you can stay on Lake Michigan? Dubbed the “Floathaus of Saugatuck,” this two-story houseboat is as nice as any landlocked rental, with white shiplap walls and spacious, impeccably decorated rooms. The hosts provide kayaks so guests can explore their watery surroundings; visit in the summer, and you can also take advantage of the marina’s communal swimming pool.
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Beaufort, North Carolina
This Beaufort cottage looks tiny from the outside, but it has a bit of a TARDIS effect once you step through the door—probably because of the 11-foot ceilings in every room. While the petite front porch and twinkle lights twisted around the living room’s wood ceiling beams are magical, the best spot in the house is easily the built-in breakfast nook, bookended by a tall window and painted a delightful shade of pea green.
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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.
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Woodstock, Vermont
Woodstock is an absurdly quaint town, and many of its buildings date back to the 1700s and 1800s. This two-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, backed by an entire wall of windows overlooking the mountains (just imagine that view in the fall). The large dining area and huge collection of books certainly don’t hurt.
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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.
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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.
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Eureka Springs, Arkansas
Eureka Springs is a tiny town tucked away in the Ozark Mountains, one of the Midwest’s most beautiful natural assets. This cabin takes full advantage of its surroundings, with a wraparound porch overlooking a stream and trees, a wood patio topped by twinkle lights, and an outdoor dining area with a fire pit and a picnic table. The one-bedroom cabin’s interior is a bright and breezy contrast, with big windows, white walls, and thoughtful touches of colorful decor.
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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?
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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).
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Lake Placid, New York
If you visit the Adirondacks and don’t stay in a log cabin, did you really even visit? This two-bedroom cabin has it all: furniture draped with sheepskin blankets, two wood-burning stoves, a large back deck with Adirondack chairs (duh), a fire pit for roasting marshmallows, and evergreens as far as the eye can see. It’s also located just two miles away from Lake Placid’s Olympic Village.
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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.
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Lake Geneva, Wisconsin
Lake Geneva is a haven for outdoor sports enthusiasts, and properties close to the water are obviously prime real estate. This downtown apartment is just steps away from the beach, and you can rent boats, jet skis, and paddleboards right across the street. The two-bedroom rental itself is a spacious and comfortable place to rest up between boat tours, and the huge second-floor porch is undoubtedly the star of the show.
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Friday Harbor, Washington
Surrounded by trees and overlooking the San Juan Channel, this mid-century modern escape is a great spot for a fun-filled yet relaxing family vacation. It features three bedrooms and spacious common areas, and the wraparound porch provides unobstructed views of the arriving ferries and boats. The house is about a five-minute drive from town, where you can visit the farmers market and great restaurants.
