Guesthouse vacation rentals in Windham County
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Top-rated guesthouse rentals in Windham County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Windham County guesthouse rentals
Family-friendly guest house rentals
Guest favorite
Guesthouse in Jamaica
4.95 out of 5 average rating, 154 reviewsThe Chick Inn
Superhost
Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviewsThe Inn at Quail Run- Guest House
Guest favorite
Guesthouse in Putney
4.95 out of 5 average rating, 333 reviewsA Vermont Carriage House
Guest favorite
Guesthouse in Brattleboro
5 out of 5 average rating, 215 reviewsLight Filled Loft in the Vermont Countryside
Guest house rentals with a patio
Superhost
Guesthouse in Wilmington
5 out of 5 average rating, 4 reviewsRenovated guest house. Min from Lake and Skiing.
Guest favorite
Private room in Newfane
4.82 out of 5 average rating, 11 reviewsYogi & artist retreat center
Guest favorite
Guesthouse in Chester
5 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
Private room in Newfane
5 out of 5 average rating, 3 reviewsQueen bed + private bath, breakfast included
Guest house rentals with a washer and dryer
Guesthouse in Wilmington
4.93 out of 5 average rating, 15 reviewsVermont Farm with beautiful views
Guesthouse in Newfane
Private Retreat, Fast Wifi Near Skiing Brattleboro
Guesthouse in Weston
4.15 out of 5 average rating, 13 reviews1BR dog-friendly mtn cabin with fireplaces
Guesthouse in Stratton
4.77 out of 5 average rating, 35 reviewsStratton Quaint Guest house
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