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Search results; Over 1,000 homes in Windsor

Top guest favourite
Cottage in Windsor
Ogden's Mill Farm
2 bedrooms, 3 beds, 1 private bathroom
16–21 Nov
,
4.97 out of 5 average rating, 466 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
Flat in Windsor
The Hideout
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Featured hotel
Room in Woodstock
Standard two queen
2 queen beds, 1 bathroom
3–8 May
New place to stay
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
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
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
Top guest favourite
Home in Windsor
Custom cabin on Mt Ascutney, with faraway views
2 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
4.97 out of 5 average rating, 137 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
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
Guest favourite
Room in Weathersfield
The Oak Room - Ladoga
1 king bed, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Flat in Weathersfield
The Loft at Weathersfield
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 195 reviews
Top guest favourite
Guest suite in Brownsville/West Windsor
Cozy Guest Suite in VT Farmhouse
1 bedroom, 1 king bed, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 214 reviews
Guest favourite
Flat in Hartland
Sunny Studio Apartment in Hartland
1 bedroom, 1 bathroom
13–18 Sept
4.88 out of 5 average rating, 501 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
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
6–11 Sept
4.88 out of 5 average rating, 106 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