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, 232 reviewsMacintosh Hill Farm
Aug 2 – 9
Guesthouse in Hanover
4.96 out of 5 average rating, 49 reviewsPrivate guest-room 1 mile from Dartmouth
Oct 1 – 8
Guesthouse in Strafford
4.93 out of 5 average rating, 137 reviewsSpacious Country Guesthouse
Oct 11 – 18
Guesthouse in Springfield
4.86 out of 5 average rating, 322 reviewsConnecticut River-Cozy Cottage
Oct 16 – 23
Guesthouse in Norwich
4.93 out of 5 average rating, 171 reviewsVermont Log Guest Home-Close to Dartmouth
Aug 30 – Sep 6
Guesthouse in Woodstock
4.98 out of 5 average rating, 209 reviewsCozy Little Spot (Self Check-in)
Aug 2 – 9
Guesthouse in Hartland
4.95 out of 5 average rating, 914 reviewsYurt In The Woods - Private Refuge
Apr 8 – 15
Guest house rentals with a patio
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsThe Lodge
Aug 23 – 30
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
Sep 20 – 27
Guesthouse in Mount Holly
4.96 out of 5 average rating, 54 reviewsMoon Acre Farm Green Mountain Oasis - near Okemo
Nov 1 – 8
Guesthouse in Hartford
4.93 out of 5 average rating, 41 reviewsAddie's Place
Jul 7 – 14
Guesthouse in Lebanon
4.96 out of 5 average rating, 45 reviewsPrivate guesthouse in Lebanon
Nov 10 – 17
Guesthouse in Reading
5.0 out of 5 average rating, 11 reviewsPeace & quiet at Comet Farm
Sep 29 – Oct 6
Guest house rentals with a washer and dryer
Guesthouse in Plymouth
4.97 out of 5 average rating, 97 reviewsQuiet Vermont Retreat near Killington and Okemo
Dec 24 – 31
Guesthouse in Andover
4.88 out of 5 average rating, 104 reviewsQuiet Self Contained Apartment in Vermont Hills
Jun 10 – 17
Guesthouse in Ludlow
5.0 out of 5 average rating, 3 reviewsThe Black Sheep Barn
Jun 22 – 29
Guesthouse in Killington
4.6 out of 5 average rating, 5 reviewsThe Apartment at the Slopeside Estate House!
Jul 15 – 22
Guesthouse in Weston
4.18 out of 5 average rating, 11 reviews1BR dog-friendly mtn cabin with fireplaces
Nov 16 – 23
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