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Search results; Over 1,000 homes in Windsor

Guest favourite
Home in Windsor
Beautiful Log Cabin with a Mountain View
3 bedrooms, 3 beds, 1 shared bathroom
17–22 Feb
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5.0 out of 5 average rating, 7 reviews
Guest favourite
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.71 out of 5 average rating, 102 reviews
Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms, 5 beds, 3 bathrooms
16–21 Sept
4.89 out of 5 average rating, 18 reviews
Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
14–19 Oct
5.0 out of 5 average rating, 20 reviews
Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms, 4 beds, 1 bathroom
15–20 Sept
4.8 out of 5 average rating, 41 reviews
Guest favourite
Cabin in Windsor
Stone cabin in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.88 out of 5 average rating, 32 reviews
Top guest favourite
Home in Hinsdale
Modern Lakehouse with Private Lake Access
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.97 out of 5 average rating, 31 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, 20 reviews
Superhost
Cabin in Plainfield
Camp on Windsor Pond Berkshires
2 bedrooms, 2 beds, 1 bathroom
15–20 Sept
4.56 out of 5 average rating, 39 reviews
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Adams
Beautiful Victorian. The heart of the Berkshires.
5 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
4.91 out of 5 average rating, 149 reviews
Top guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
5 bedrooms, 7 beds, 2.5 bathrooms
22–27 Sept
4.93 out of 5 average rating, 212 reviews
Top guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in North Adams
See MoCA from your mansion+Sauna!
4 bedrooms, 4 beds, 1 bathroom
26–31 Oct
4.97 out of 5 average rating, 730 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
15–20 Sept
4.97 out of 5 average rating, 78 reviews
Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
4.81 out of 5 average rating, 166 reviews
Superhost
Apartment in Adams
Downtown Adams Vintage Getaway
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.74 out of 5 average rating, 68 reviews
Guest favourite
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Home in Hancock
Grand 6BR Home by Jiminy | Hike • Hot Tub • Games
6 bedrooms, 14 beds, 5.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 64 reviews