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Search results; Over 1,000 homes in Windsor

Guest favourite
Cabin in Windsor
Stone cabin in the Berkshires
2 bedrooms, 3 beds, 1 private bathroom
12–17 Sept
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4.88 out of 5 average rating, 32 reviews
Guest favourite
Home in Windsor
Beautiful Log Cabin with a Mountain View
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.7 out of 5 average rating, 99 reviews
Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.8 out of 5 average rating, 41 reviews
Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.88 out of 5 average rating, 17 reviews
Top guest favourite
Home in Adams
Beautiful Victorian. The heart of the Berkshires.
5 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
4.91 out of 5 average rating, 149 reviews
Superhost
Cabin in Plainfield
Camp on Windsor Pond Berkshires
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.55 out of 5 average rating, 38 reviews
Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Hinsdale
Modern Lakehouse with Private Lake Access
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms, 5 beds, 1 bathroom
5–10 Oct
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.81 out of 5 average rating, 165 reviews
Top guest favourite
Home in Hinsdale
Hummingbird Haven
5 bedrooms, 6 beds, 3.5 bathrooms
2–7 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
4.96 out of 5 average rating, 55 reviews
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Sept
New place to stay
Home in Charlemont
3 Bedroom 2 Bath Cottage on The Brook
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
New place to stay
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 76 reviews
Top guest favourite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 42 reviews