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.

Guest favorite
Tiny home in Wilmington
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!
Aug 13 – 20
$192 per night
4.98 out of 5 average rating, 117 reviews
Guest favorite
Cabin in Jamaica
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.
Jun 10 – 17
$115 per night
4.99 out of 5 average rating, 177 reviews
Guest favorite
Barn in Marlboro
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 5 – 12
$122 per night
4.95 out of 5 average rating, 258 reviews

Popular amenities for Windham County tiny house rentals

Family-friendly tiny house rentals

Guest favorite
Tiny home in Jamaica
Forest Cabin ~ 7min to Stratton, Cozy, Private
May 12 – 19
$75 per night
4.89 out of 5 average rating, 340 reviews
Guest favorite
Tiny home in Putney
Honeycrisp Cottage - A Tiny Timber Frame
Aug 6 – 13
$207 per night
4.95 out of 5 average rating, 661 reviews
Guest favorite
Cabin in Londonderry
Stone Fence Cabin
Oct 7 – 14
$91 per night
4.93 out of 5 average rating, 308 reviews
Guest favorite
Cottage in Dover
Open again 5/1/24 Summer cottage in the woods
Jun 3 – 10
$103 per night
4.95 out of 5 average rating, 216 reviews
Guest favorite
Cabin in Newfane
Riverrun Cottage
Jun 27 – Jul 4
$169 per night
4.93 out of 5 average rating, 188 reviews
Superhost
Cabin in Londonderry
Art Studio Barn - hot tub & sauna access #1 Airbb
Nov 18 – 25
$276 per night
4.75 out of 5 average rating, 349 reviews
Guest favorite
Cabin in Brookline
Last Frontier Log Cabin
Sep 13 – 20
$160 per night
5.0 out of 5 average rating, 45 reviews
Guest favorite
Cabin in Londonderry
Quaint cottage near 4 ski resorts
Jan 24 – 31
$175 per night
4.95 out of 5 average rating, 74 reviews
Superhost
Tiny home in Jamaica
Brookside Cabin ~ 7min to Stratton, Private, Views
May 5 – 12
$97 per night
4.89 out of 5 average rating, 236 reviews
Superhost
Cabin in South Londonderry
Fernando’s picturesque hideaway - Lovebirds Cabin
May 2 – 9
$159 per night
4.64 out of 5 average rating, 381 reviews

Tiny house rentals with a patio

Guest favorite
Tiny home in Brattleboro
"Mountain View" Hike In Cabin Retreat
Dec 9 – 16
$83 per night
4.95 out of 5 average rating, 172 reviews
Superhost
Tiny home in Wilmington
The Pines Cabin | New Tiny Home Near Mt Snow!
Jun 18 – 25
$158 per night
4.8 out of 5 average rating, 15 reviews
Guest favorite
Cabin in Brattleboro
Quintessential Vermont Cabin
May 24 – 29
$130 per night
4.86 out of 5 average rating, 7 reviews
Guest favorite
Treehouse in Putney
Treehouse Haven in Putney in All Seasons
Oct 2 – 9
$251 per night
5.0 out of 5 average rating, 51 reviews
Guest favorite
Treehouse in Newfane
Idyllic getaway with wrap-around deck
Aug 16 – 23
$299 per night
4.94 out of 5 average rating, 32 reviews
Guest favorite
Tiny home in Putney
~Luxury Tiny Cabin~
Jul 3 – 10
$193 per night
5.0 out of 5 average rating, 10 reviews
Home in Jamaica
Rooted Moon Retreat…Sun filled cabin in the forest
Jun 2 – 9
$197 per night
4.82 out of 5 average rating, 68 reviews
Camper/RV in Stratton
Bambi Inn Jamaica
Sep 14 – 21
$141 per night
5.0 out of 5 average rating, 4 reviews
Resort in Guilford
Vikings Villages Resort - Double Bed Room
Sep 14 – 21
$298 per night
5.0 out of 5 average rating, 4 reviews
Superhost
Tiny home in Brattleboro
“Sugar Maple” Rustic Cabin Getaway with Fireplace
May 15 – 22
$84 per night
4.86 out of 5 average rating, 164 reviews
Guest favorite
Tiny home in Brattleboro
“Hickory” Rustic Cabin Retreat with Fireplace
Dec 30 – Jan 6
$91 per night
4.94 out of 5 average rating, 140 reviews

Tiny house rentals with outdoor seating

Guest favorite
Guesthouse in Brattleboro
Mahalo Temple Retreat
May 6 – 13
$82 per night
4.93 out of 5 average rating, 414 reviews
Guest favorite
Home in Winhall
Modern Cabin with Hot Tub & EV Charging Station
Aug 11 – 18
$357 per night
4.98 out of 5 average rating, 120 reviews
Guest favorite
Cabin in Guilford
Serenity Now - Couples Retreat or Writer's Dream
Sep 2 – 9
$162 per night
4.96 out of 5 average rating, 472 reviews
Guest favorite
Cabin in Townshend
Solar Cabin at Big Picture Farm
Apr 21 – 28
$262 per night
4.98 out of 5 average rating, 129 reviews
Guest favorite
Tiny home in Wardsboro
Little Red House Vermont
Apr 1 – 8
$153 per night
4.94 out of 5 average rating, 283 reviews
Guest favorite
Cottage in Londonderry
Vermont Treehouse - Romantic Private Elegant
Sep 16 – 23
$293 per night
4.96 out of 5 average rating, 199 reviews
Guest favorite
Cabin in Jamaica
Jamaica Mod A Frame
Jun 12 – 19
$239 per night
4.9 out of 5 average rating, 129 reviews
Guest favorite
Cabin in Winhall
A-Frame Mountain Retreat near Manchester
Jul 19 – 26
$297 per night
4.96 out of 5 average rating, 283 reviews
Superhost
Cabin in Brattleboro
Solar Cabin Farmstay
May 11 – 18
$96 per night
4.93 out of 5 average rating, 45 reviews
Guest favorite
Tiny home in Townshend
Cheerful cabin retreat in the woods and mountains
Apr 22 – 29
$127 per night
4.98 out of 5 average rating, 40 reviews
Guest favorite
Tiny home in Athens
LUXE Forest Retreat
Jun 14 – 21
$279 per night
4.91 out of 5 average rating, 23 reviews
Guest favorite
Guesthouse in Grafton
VT Sugar House-Guesthouse
Oct 8 – 15
$63 per night
4.91 out of 5 average rating, 86 reviews

Destinations to explore