Guest house holiday rentals in Windham County
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Top-rated guest house rentals in Windham County
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
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Popular amenities for guest house rentals in Windham County
Family-friendly guest house rentals
Guest house in Wilmington
4.96 out of 5 average rating, 24 reviewsThe Inn at Quail Run- Guest House
27 Mar – 3 Apr
Guest house in Chesterfield
5.0 out of 5 average rating, 22 reviews1790 Historic Home in Chesterfield for Five Guests
15–22 Jul
Guest house in Putney
4.95 out of 5 average rating, 322 reviewsA Vermont Carriage House
13–20 Dec
Guest house in Jamaica
4.95 out of 5 average rating, 133 reviewsThe Chick Inn
5–12 Jun
Guest house in Brattleboro
4.99 out of 5 average rating, 199 reviewsLight Filled Loft in the Vermont Countryside
3–10 Jul
Guest house rentals with a patio
Guest house in Chester
5.0 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
15–22 Sep
Guest house in Newfane
5.0 out of 5 average rating, 3 reviewsQueen bed + private bath, breakfast included
15–22 Oct
Guest house in Wilmington
5.0 out of 5 average rating, 3 reviewsRenovated guest house. Min from Lake and Skiing.
22–29 Aug
Guest house in Newfane
4.8 out of 5 average rating, 10 reviewsYogi & artist retreat center
29 May – 5 Jun
Guest house rentals with a washing machine and dryer
Guest house in Stratton
4.77 out of 5 average rating, 35 reviewsStratton Quaint Guest house
29 Jul – 5 Aug
Guest house in Wilmington
4.93 out of 5 average rating, 15 reviewsVermont Farm with beautiful views
26 Jun – 3 Jul
Guest house in Weston
4.2 out of 5 average rating, 10 reviews1BR dog-friendly mtn cabin with fireplaces
6–13 Sep
Guest house in Marlboro
4.99 out of 5 average rating, 140 reviewsRefined, serene and like no other, Marlboro, VT.
12–19 Jan
Guest house in Jamaica
4.86 out of 5 average rating, 56 reviews5 min to Stratton, pet friendly, fire pit
17–24 Jun
Guest house in Wilmington
5.0 out of 5 average rating, 3 reviewsRenovated guest house. Min from Lake and Skiing.
22–29 Aug
Guest house in Town of Rockingham
5.0 out of 5 average rating, 11 reviewsPeaceful Historic Cottage
27 Sep – 4 Oct
Guest house in Wilmington
4.91 out of 5 average rating, 57 reviewsNew! remodeled Barn. min from Lake, Ski, Hot tub
9–16 Jul
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