Guesthouse vacation rentals in Windsor County
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Top-rated guesthouse rentals in Windsor County
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor County guesthouse rentals
Family-friendly guest house rentals
Guest favorite
Guesthouse in Randolph
4.96 out of 5 average rating, 233 reviewsMacintosh Hill Farm
Guest favorite
Guesthouse in Hanover
4.96 out of 5 average rating, 49 reviewsPrivate guest-room 1 mile from Dartmouth
Guest favorite
Guesthouse in Norwich
4.93 out of 5 average rating, 171 reviewsVermont Log Guest Home-Close to Dartmouth
Guest favorite
Guesthouse in Springfield
4.86 out of 5 average rating, 325 reviewsConnecticut River-Cozy Cottage
Guest favorite
Guesthouse in Hartland
4.95 out of 5 average rating, 917 reviewsYurt In The Woods - Private Refuge
Guest favorite
Guesthouse in Woodstock
4.98 out of 5 average rating, 209 reviewsCozy Little Spot (Self Check-in)
Guest house rentals with a patio
Guest favorite
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsThe Lodge
Guest favorite
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
Guest favorite
Guesthouse in Mount Holly
4.96 out of 5 average rating, 55 reviewsMoon Acre Farm Green Mountain Oasis - near Okemo
Guest favorite
Guesthouse in Hartford
4.91 out of 5 average rating, 46 reviewsAddie's Place
Guest favorite
Guesthouse in Lebanon
4.96 out of 5 average rating, 48 reviewsPrivate guesthouse in Lebanon
Guest favorite
Guesthouse in Reading
5.0 out of 5 average rating, 11 reviewsPeace & quiet at Comet Farm
Guest house rentals with a washer and dryer
Guest favorite
Guesthouse in Plymouth
4.97 out of 5 average rating, 97 reviewsQuiet Vermont Retreat near Killington and Okemo
Guesthouse in Ludlow
5.0 out of 5 average rating, 3 reviewsThe Black Sheep Barn
Guesthouse in Killington
4.6 out of 5 average rating, 5 reviewsThe Apartment at the Slopeside Estate House!
Guesthouse in Weston
4.18 out of 5 average rating, 11 reviews1BR dog-friendly mtn cabin with fireplaces
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