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 Hartland
4.95 out of 5 average rating, 912 reviewsYurt In The Woods - Private Refuge
Feb 24 – Mar 3
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, 48 reviewsPrivate guest-room 1 mile from Dartmouth
Aug 19 – 26
Guesthouse in Strafford
4.93 out of 5 average rating, 137 reviewsSpacious Country Guesthouse
Oct 8 – 15
Guesthouse in Springfield
4.86 out of 5 average rating, 321 reviewsConnecticut River-Cozy Cottage
Jan 21 – 28
Guesthouse in Norwich
4.93 out of 5 average rating, 171 reviewsVermont Log Guest Home-Close to Dartmouth
Sep 29 – Oct 6
Guesthouse in Woodstock
4.98 out of 5 average rating, 206 reviewsCozy Little Spot (Self Check-in)
Dec 11 – 18
Guest house rentals with a patio
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsThe Lodge
Aug 17 – 24
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
Sep 12 – 19
Guesthouse in Mount Holly
4.96 out of 5 average rating, 54 reviewsMoon Acre Farm Green Mountain Oasis - near Okemo
Oct 26 – Nov 2
Guesthouse in Hartford
4.93 out of 5 average rating, 40 reviewsAddie's Place
Jun 15 – 22
Guesthouse in Lebanon
4.95 out of 5 average rating, 43 reviewsPrivate guesthouse in Lebanon
Nov 10 – 17
Guesthouse in Reading
5.0 out of 5 average rating, 11 reviewsPeace & quiet at Comet Farm
Sep 8 – 15
Guest house rentals with a washer and dryer
Guesthouse in Cavendish
5.0 out of 5 average rating, 7 reviewsBrand New Village home in Cavendish, VT
Jul 4 – 11
Guesthouse in Andover
4.88 out of 5 average rating, 104 reviewsQuiet Self Contained Apartment in Vermont Hills
Jun 3 – 10
Guesthouse in Ludlow
5.0 out of 5 average rating, 3 reviewsThe Black Sheep Barn
Jul 25 – Aug 1
Guesthouse in Killington
4.6 out of 5 average rating, 5 reviewsThe Apartment at the Slopeside Estate House!
Jun 5 – 12
Guesthouse in Weston
4.2 out of 5 average rating, 10 reviews1BR dog-friendly mtn cabin with fireplaces
Nov 2 – 9
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