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Vacation rentals in Windham County

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Top-rated vacation rentals in Windham County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Guest suite in Brattleboro
Charming studio in renovated 19th century church.
This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it. COMING NEW KITCHEN PHOTO!
Oct 31 – Nov 7
$81 per night
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 25 – Dec 2
$122 per night
Guest favorite
Cottage in Newfane
Ridgeview: Cozy Cottage with a View
COVID-19 NOTICE: We are open for bookings! And Vermont is a good place to be right now, and always. So you know, we observe the cleaning and safety guidelines required by the State and Air B&B. More about that upon request. At "Ridgeview" you can go to sleep to the flicker of a wood stove, wake up to sunshine streaming through tall windows onto honey-colored pine flooring, and watch from your deck as sunlight fills the river valley and plays across the ridge opposite.
Sep 5 – 12
$121 per night

Popular amenities for Windham County vacation rentals

Other great vacation rentals in Windham County

Guest favorite
Tiny home in Wilmington
Beautiful Timber Frame Retreat
Jul 17 – 24
$189 per night
Guest favorite
Guest suite in Newfane
Cute studio apt on lovely historic VT farm
Dec 10 – 17
$86 per night
Guest favorite
Home in Putney
Cozy Train Depot in Putney Vermont
Mar 22 – 29
$97 per night
Guest favorite
Cabin in Newfane
Great Views, Mount Snow, Hot Tub, Private
Dec 25 – Jan 1
$256 per night
Guest favorite
Cabin in Putney
Vermont Retreat Cottage| Cozy & Romantic Escape
Apr 13 – 20
$190 per night
Guest favorite
Cottage in Newfane
Cozy Vermont Antique Sugar House with Fireplace
Jan 28 – Feb 4
$135 per night
Cabin in Jamaica
Green Mountain Modern House: iconic modern getaway
May 8 – 15
$438 per night
Guest favorite
Treehouse in Brookline
Flower Farm Glamping w/ Wood-Fired Hot Tub
Jan 22 – 29
$263 per night
Guest favorite
Chalet in Jamaica
Vermont Chalet
Apr 25 – May 2
$215 per night
Guest favorite
Guesthouse in Brattleboro
Mahalo Temple Retreat
May 4 – 11
$83 per night
Guest favorite
Cabin in Jamaica
New Cabin in Jamaica
Apr 22 – 29
$115 per night
Guest favorite
Home in Putney
Vermont Botanical Studio Apartment
Nov 4 – 11
$89 per night

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