Guesthouse vacation rentals in Windsor County
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Top-rated guesthouse rentals in Windsor 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 Windsor County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Randolph
4.96 out of 5 average rating, 246 reviewsMacintosh Hill Farm
Guesthouse in Strafford
4.93 out of 5 average rating, 142 reviewsSpacious Country Guesthouse
Guesthouse in Chester
4.92 out of 5 average rating, 169 reviewsChester Carriage House-Historic-20 Min to Okemo
Guesthouse in Woodstock
4.98 out of 5 average rating, 231 reviewsCozy Little Spot (Self Check-in)
Guesthouse in Springfield
4.86 out of 5 average rating, 349 reviewsConnecticut River-Cozy Cottage
Guesthouse in Hartland
4.95 out of 5 average rating, 956 reviewsYurt In The Woods - Private Refuge
Guesthouse in Norwich
4.94 out of 5 average rating, 201 reviewsVermont Log Guest Home-Close to Dartmouth
Guesthouse in Hanover
4.96 out of 5 average rating, 57 reviewsPrivate guest-room 1 mile from Dartmouth
Guest house rentals with a patio
Guesthouse in Mount Holly
4.95 out of 5 average rating, 63 reviewsMoon Acre Farm Green Mountain Oasis - near Okemo
Guesthouse in Hartford
4.9 out of 5 average rating, 86 reviewsAddie's Place
Guesthouse in Lebanon
4.93 out of 5 average rating, 76 reviewsPrivate guesthouse in Lebanon
Guesthouse in Reading
5 out of 5 average rating, 22 reviewsPeace & quiet at Comet Farm
Guesthouse in Chester
4.94 out of 5 average rating, 16 reviewsThe Lodge
Guesthouse in Chester
5 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
Guest house rentals with a washer and dryer
Guesthouse in Killington
4.6 out of 5 average rating, 5 reviewsThe Apartment at the Slopeside Estate House!
Guesthouse in Andover
4.88 out of 5 average rating, 104 reviewsQuiet Self Contained Apartment in Vermont Hills
Guesthouse in Weston
4.15 out of 5 average rating, 13 reviews1BR dog-friendly mtn cabin with fireplaces
Guesthouse in Plymouth
4.97 out of 5 average rating, 97 reviewsQuiet Vermont Retreat near Killington and Okemo
Guesthouse in Cavendish
5 out of 5 average rating, 11 reviewsBrand New Village home in Cavendish, VT
Guesthouse in Ludlow
5 out of 5 average rating, 5 reviewsThe Black Sheep Barn
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