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Search results; Over 1,000 homes in Windsor

Top guest favourite
Home in Windsor
Custom cabin on Mt Ascutney, with faraway views
2 bedrooms, 5 beds, 2 private bathrooms
17–22 Oct
,
4.97 out of 5 average rating, 137 reviews
Top guest favourite
Flat in Windsor
Charming apartment on the Windsor Green
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 29 reviews
Featured hotel
Room in Woodstock
Standard two queen
2 queen beds, 1 bathroom
3–8 May
New place to stay
Top guest favourite
Cottage in Windsor
Ogden's Mill Farm
2 bedrooms, 3 beds, 1 bathroom
16–21 Nov
4.97 out of 5 average rating, 466 reviews
Flat in Windsor
The Hideout
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Windsor
Charming Cabin in Central VT
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Cornish
Country Home next to Covered Bridge
3 bedrooms, 4 beds, 1.5 bathrooms
23–28 Oct
4.96 out of 5 average rating, 166 reviews
Top guest favourite
Cabin in Weathersfield
A-Frame | Ski/Hike | Dog-Friendly | New Back Deck
2 bedrooms, 3 beds, 1.5 bathrooms
7–13 Sept
5.0 out of 5 average rating, 49 reviews
Guest favourite
Bed and breakfast in Windsor
Stay at the largest Colonial Revival Mansion in US
1 bedroom, 2 beds, 1.5 bathrooms
7–12 Sept
4.89 out of 5 average rating, 93 reviews
Guest favourite
Townhouse in West Windsor
Mountain Edge Living
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Oct
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Home in Cavendish
Midcentury Hillside Retreat - Summer Paradise
3 bedrooms, 6 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 134 reviews
Guest favourite
Home in Hartland
19th Century Bohemian Barn House
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 103 reviews
Top guest favourite
Cabin in West Windsor
Cowshed Cabin Farm
2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Apr
4.96 out of 5 average rating, 150 reviews
Guest favourite
Home in West Windsor
Tranquility Farm 2
3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in West Windsor
Gorgeous and Secluded Log Home near Woodstock, Vt
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
4.97 out of 5 average rating, 76 reviews
Top guest favourite
Cabin in Weathersfield
Little Ascutney Post &Beam Chalet -Cozy near Okemo
2 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 41 reviews
Guest favourite
Room in Windsor
Stay at the Largest Colonial Revival Mansion in US
1 queen bed, 1.5 bathrooms
5–10 Sept
4.88 out of 5 average rating, 106 reviews
Top guest favourite
Guest suite in Windsor
Charming Brick Cape near Windsor Grasslands area.
1 bedroom, 2 beds, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 114 reviews
Top guest favourite
Room in Windsor
Fangs and Fuzz Room At All Hallows Inn B and B
1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 59 reviews