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Search results; Over 1,000 homes in Windsor

Top guest favourite
Guest suite in Windsor
Charming Brick Cape near Windsor Grasslands area.
1 bedroom, 2 beds, 1 private bathroom
1–6 Oct
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4.97 out of 5 average rating, 114 reviews
Top guest favourite
Cottage in Windsor
Ogden's Mill Farm
4.97 out of 5 average rating, 455 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Nov
Top guest favourite
Home in Windsor
Stylish Vermont Cabin | Views · Trails · Luxe
4.98 out of 5 average rating, 129 reviews, 2 bedrooms, 5 beds, 2 bathrooms
20–25 Jul
Top guest favourite
Flat in Windsor
Charming apartment on the Windsor Green
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in West Windsor
Elm Gate Farm
5.0 out of 5 average rating, 35 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Sept
Top guest favourite
Home in West Windsor
Chuck's Place
4.95 out of 5 average rating, 86 reviews, 3 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Place to stay in Cornish
"Blue Room"—Fernald Hill Farm/Yatsevitch Forest
4.97 out of 5 average rating, 76 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Guest favourite
Cabin in West Windsor
Peaceful Vermont Cottage w/ Outdoor Sauna!
4.83 out of 5 average rating, 78 reviews, 3 bedrooms, 4 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Tiny home in Hartland
Cabin on the Hill
4.97 out of 5 average rating, 232 reviews, 1 bedroom, 2 beds, No bathroom
23–28 Aug
Top guest favourite
Home in West Windsor
Birdie's Nest Guesthouse
4.98 out of 5 average rating, 181 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Guest house in Hartland
Cozy - Killington 40 min. Woodstock-Hanover-Piano!
4.97 out of 5 average rating, 206 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Aug
Top guest favourite
Cottage in Hartland
Cottage 5 miles from Woodstock-Dog Friendly w/FIOS
4.94 out of 5 average rating, 163 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Bed and breakfast in Windsor
Stay at the largest Colonial Revival Mansion in US
4.89 out of 5 average rating, 91 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
4–9 Jul
Top guest favourite
Home in Cornish
Cornish-Windsor Bridge Retreat with Amazing Views
4.94 out of 5 average rating, 35 reviews, 6 bedrooms, 9 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Barn in Woodstock
THE LOFT, stunning views from a timber framed barn
4.99 out of 5 average rating, 309 reviews, 2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
Top guest favourite
Cabin in West Windsor
Designer Cabin Firepit Trails Near Woodstock, GMHA
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
Top guest favourite
Home in West Windsor
Meadow View. 35 acres outside your door!
4.98 out of 5 average rating, 231 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Farm stay in Baltimore
Hawk Mtn Farm's lovely one bedroom apartment!
4.94 out of 5 average rating, 137 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
Guest favourite
Room in Cornish
Fitch Family Farm
4.91 out of 5 average rating, 172 reviews, 1 queen bed, 1 bathroom
15–20 Jul