Tiny house vacation rentals in Windham County

Find and book unique tiny house rentals on Airbnb

Top-rated tiny house rentals in Windham County

Guests agree: these tiny house rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Londonderry

4.94 out of 5 average rating, 334 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Guest favorite

Bungalow in Brattleboro

4.94 out of 5 average rating, 249 reviews

Healix Luxury Getaway

This charming turn of the century cottage has been mindfully renovated with radiant floor heat and indirect lighting. The space includes vaulted ceilings, large skylight, abundant oxygen providing greenery, and high end bathroom appointments. Previously a yoga studio, it is solely an airbnb now. It's conveniently located off exit 1 on I-91, within walking distance of quaint downtown Brattleboro, with safe and free off-street parking. An entry ramp provides ease of accessibility for all.

Guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 203 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Guest favorite

Home in Winhall

4.95 out of 5 average rating, 190 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Just minutes to skiing at Stratton Mountain, Bromley and Magic. Explore 27+ acres of forest with trails, river, sculpture gardens and private pond. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. A short drive to Manchester with shops and restaurants. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Guest favorite

Cabin in Jamaica

5 out of 5 average rating, 215 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Guest favorite

Tiny home in Dover

4.99 out of 5 average rating, 166 reviews

Rustic Cabin in foothills of Green Mountains

Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 483 reviews

Mahalo Temple Retreat

Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

Guest favorite

Tiny home in Putney

4.94 out of 5 average rating, 109 reviews

Cottage core dreamland A woodland retreat

Come enjoy our cozy cottage in the vermont woods on 16 acres. this unique space invokes a peaceful serenity while being amongst the trees. It is a stand alone unit on the same property as the owners, with dogs and free range chickens. There is a back deck to have your privacy and space to have a fire. In this 350 square foot tiny home There is even a kitchen and bathroom with a small stand up shower. There is a loft for sleeping so you must feel comfortable climbing up and down a ladder.

Superhost

Tiny home in Brattleboro

4.83 out of 5 average rating, 101 reviews

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

Guest favorite

Chalet in Jamaica

4.98 out of 5 average rating, 241 reviews

Vermont Chalet

Escape to our cozy A-frame on 3 private acres in Southern Vermont for a peaceful, secluded retreat. Relax to the soothing sounds of the river across the street while unwinding on the covered, screened-in porch. Enjoy a fully stocked kitchen, updated bathroom, strong WiFi, video games and books by a warm wood stove. Explore local towns, hike, or wander through our tranquil forest. With an EV charger, local artisan soaps, and warm woodstove, this is the perfect spot for a serene getaway.

Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 290 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Guest favorite

Cabin in Putney

4.9 out of 5 average rating, 125 reviews

Cabin getaway in Southern Vermont

Let us share our little piece of Vermont with you! Located off a dirt road, tucked into a corner of our working homestead, you'll find a space to relax, unwind, and reconnect. This cabin has everything you need for a private and comfortable escape. Downstairs you’ll find a comfortable leather couch, small kitchen, & bathroom with vanity & shower. The bedroom (located upstairs) has a queen sized bed. All linens provided.