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Guesthouse vacation rentals in Windham County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Windham County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Windham County guesthouse rentals
Family-friendly guest house rentals
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Guesthouse in Chesterfield
5 out of 5 average rating, 22 reviews1790 Historic Home in Chesterfield for Five Guests
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Guesthouse in Putney
4.94 out of 5 average rating, 325 reviewsA Vermont Carriage House
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Guesthouse in Jamaica
4.95 out of 5 average rating, 135 reviewsThe Chick Inn
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Guesthouse in Brattleboro
5 out of 5 average rating, 202 reviewsLight Filled Loft in the Vermont Countryside
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Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviewsThe Inn at Quail Run- Guest House
Guest house rentals with a patio
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Guesthouse in Chester
5 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
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Guesthouse in Guilford
Beech Cottage Vermont
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Private room in Newfane
5 out of 5 average rating, 3 reviewsQueen bed + private bath, breakfast included
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Private room in Newfane
4.82 out of 5 average rating, 11 reviewsYogi & artist retreat center
Guest house rentals with a washer and dryer
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Guesthouse in Stratton
4.77 out of 5 average rating, 35 reviewsStratton Quaint Guest house
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Guesthouse in Wilmington
4.93 out of 5 average rating, 15 reviewsVermont Farm with beautiful views
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Guesthouse in Weston
4.18 out of 5 average rating, 11 reviews1BR dog-friendly mtn cabin with fireplaces
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Guesthouse in Marlboro
4.99 out of 5 average rating, 142 reviewsRefined, serene and like no other, Marlboro, VT.
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Guesthouse in Jamaica
4.86 out of 5 average rating, 57 reviews5 min to Stratton, pet friendly, fire pit
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Guesthouse in Town of Rockingham
4.94 out of 5 average rating, 17 reviewsPeaceful Historic Cottage
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Guesthouse in Wilmington
4.92 out of 5 average rating, 59 reviewsNew! remodeled Barn. min from Lake, Ski, Hot tub
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Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviewsThe Inn at Quail Run- Guest House
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