Guesthouse vacation rentals in Windham County
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Top-rated guesthouses in Windham County
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Windham County guesthouses
Family-friendly guesthouses
Superhost
Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviewsThe Inn at Quail Run- Guest House
Guesthouse in Chesterfield
5.0 out of 5 average rating, 22 reviews1790 Historic Home in Chesterfield for Five Guests
Guest favourite
Guesthouse in Jamaica
4.95 out of 5 average rating, 133 reviewsThe Chick Inn
Guest favourite
Guesthouse in Brattleboro
5.0 out of 5 average rating, 200 reviewsLight Filled Loft in the Vermont Countryside
Guest favourite
Guesthouse in Putney
4.95 out of 5 average rating, 324 reviewsA Vermont Carriage House
Guesthouses with a patio
Guest favourite
Guesthouse in Wilmington
5.0 out of 5 average rating, 23 reviewsCozy, charming cottage 7 mins from Mount Snow
Guest favourite
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
Superhost
Guesthouse in Newfane
5.0 out of 5 average rating, 3 reviewsQueen bed + private bath, breakfast included
Superhost
Guesthouse in Newfane
4.8 out of 5 average rating, 10 reviewsYogi & artist retreat center
Guesthouse rentals with a washer and dryer
Guesthouse in Stratton
4.77 out of 5 average rating, 35 reviewsStratton Quaint Guest house
Guest favourite
Guesthouse in Wilmington
4.93 out of 5 average rating, 15 reviewsVermont Farm with beautiful views
Guesthouse in Weston
4.18 out of 5 average rating, 11 reviews1BR dog-friendly mtn cabin with fireplaces
Guest favourite
Guesthouse in Wilmington
4.91 out of 5 average rating, 58 reviewsNew! remodeled Barn. min from Lake, Ski, Hot tub
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