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

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. 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!

Nov 5 – 12

G$21,416 GYD per night

Guest favorite

Tiny home in Jamaica

4.88 out of 5 average rating, 345 reviews

Forest Cabin ~ 7min to Stratton, Cozy, Private

Authentic Vermont post and beam cabin is 3 miles from Stratton's Sun Bowl, a short 7 minute drive away. Swimming at the brook on the property. Dogs are welcome, $30 fee per dog. Sorry, no cats due to allergies. Vinyl record player & records, VHS & videos. Full kitchen. Satellite Internet/WiFi 20-100 mbps. The bathroom has a composting toilet - it is odorless and easy to use. Heat options: 2 gas wall furnaces, wood-stove & pellet stove. Front porch, picnic table, fire pit & propane BBQ grill.

May 20 – 27

G$26,308 GYD per night

Guest favorite

Bungalow in Brattleboro

4.93 out of 5 average rating, 232 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.

Jun 18 – 25

G$30,412 GYD per night

Guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 140 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!

Sep 4 – 11

G$44,405 GYD per night

Guest favorite

Cabin in Jamaica

4.99 out of 5 average rating, 185 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.

Jul 28 – Aug 4

G$30,771 GYD per night

Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 430 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.

Jul 7 – 14

G$21,343 GYD per night

Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 263 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.

Nov 13 – 20

G$29,310 GYD per night

Guest favorite

Cabin in Newfane

5.0 out of 5 average rating, 150 reviews

Custom cabin by the river in Newfane, VT

OPEN mid-MAY-OCTOBER. Our beautiful one-room custom cabin is on the edge of the woods surrounded by the Rock River. It's freshly appointed, with a king-size bed, is spotlessly clean and very romantic. The cabin has simple cooking facilities (details below) and an outdoor grill, twinkle lights on the deck, hammock, and 2 fire-pits, one by the cabin, and one on the beach. One COMPLIMENTARY BREAKFAST is included, with homemade popovers, fresh out of the oven. A smoke-free property.

Jan 7 – 14

G$29,955 GYD per night

Guest favorite

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

-The Ice Pond Camp, East Dover, VT. Small well equipped country cottage, surrounded by nature & quaint beauty. Enjoy the lovely Southern Vermont seasons as you relax, disconnect, recharge & spend your days living a slower pace - surrounded by authentic rural beauty. Close to Wilmington and West Dover, (home of Mount Snow) and towns such as Putney and Brattleboro. Just minutes away are scenic villages, green farms, brooks,ponds and lakes, walking trails & country roads.

Jul 19 – 26

G$25,965 GYD per night

Guest favorite

Tiny home in Dover

4.99 out of 5 average rating, 150 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. Most seasons, walk to cabin is 80 ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Dec 22 – 29

G$24,168 GYD per night

Guest favorite

Cabin in Townshend

4.98 out of 5 average rating, 130 reviews

Solar Cabin at Big Picture Farm

Nestled into the hillside of our 100 acre farm, the Solar Cabin at Big Picture Farm is a brand new cabin. Featuring a light, airy and modern feel the cabin is a great respite. Enjoy the views from the large windows, the soft king size bed with luxury Matouk Linens, lounge on the sofa by the gas fireplace, or simply cook yourself a meal in the elegant kitchen. This is a perfect place to come to enjoy the wilderness and tranquility of southern Vermont.

Jul 15 – 22

G$62,580 GYD per night

Guest favorite

Tiny home in Putney

4.95 out of 5 average rating, 671 reviews

Honeycrisp Cottage - A Tiny Timber Frame

Honeycrisp Cottage a Tiny Timber Frame is a bright, energy-efficient dwelling nestled on 9 acres overlooking a beautiful forested mountain & trails to explore along a brook. A peaceful getaway retreat equipped with a living room, a king bed, a loft with a queen bed, a full kitchen, & a full bathroom. *Please No Smoking On The Property Mt. Snow - 50 mins Okemo - 50 mins Stratton - 1 hr Killington - 1 hr 20 mins

Dec 29 – Jan 5

G$45,571 GYD per night