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
Get the amount of space that is right for you
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 4 – 11
Guesthouse in Hanover
4.96 out of 5 average rating, 49 reviewsPrivate guest-room 1 mile from Dartmouth
Oct 21 – 28
Guesthouse in Strafford
4.93 out of 5 average rating, 137 reviewsSpacious Country Guesthouse
Sep 17 – 24
Guesthouse in Springfield
4.86 out of 5 average rating, 322 reviewsConnecticut River-Cozy Cottage
Jan 28 – Feb 4
Guesthouse in Woodstock
4.98 out of 5 average rating, 209 reviewsCozy Little Spot (Self Check-in)
Jan 29 – Feb 5
Guesthouse in Norwich
4.93 out of 5 average rating, 171 reviewsVermont Log Guest Home-Close to Dartmouth
Aug 30 – Sep 6
Guesthouse in Hartland
4.95 out of 5 average rating, 914 reviewsYurt In The Woods - Private Refuge
Nov 11 – 18
Guest house rentals with a patio
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsThe Lodge
Aug 24 – 31
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
Sep 21 – 28
Guesthouse in Mount Holly
4.96 out of 5 average rating, 54 reviewsMoon Acre Farm Green Mountain Oasis - near Okemo
Sep 3 – 10
Guesthouse in Lebanon
4.96 out of 5 average rating, 46 reviewsPrivate guesthouse in Lebanon
Jun 9 – 16
Guesthouse in Hartford
4.93 out of 5 average rating, 42 reviewsAddie's Place
Jul 23 – 30
Guesthouse in Reading
5.0 out of 5 average rating, 11 reviewsPeace & quiet at Comet Farm
Oct 1 – 8
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 11 – 18
Guesthouse in Ludlow
5.0 out of 5 average rating, 3 reviewsThe Black Sheep Barn
Oct 19 – 26
Guesthouse in Killington
4.6 out of 5 average rating, 5 reviewsThe Apartment at the Slopeside Estate House!
Jun 5 – 12
Guesthouse in Weston
4.18 out of 5 average rating, 11 reviews1BR dog-friendly mtn cabin with fireplaces
Nov 18 – 25
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