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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
Guest favourite
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.7 out of 5 average rating, 100 reviews
Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
4.89 out of 5 average rating, 18 reviews
Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms, 4 beds, 1 bathroom
9–14 Sept
4.8 out of 5 average rating, 41 reviews
Top guest favourite
Home in Adams
Beautiful Victorian. The heart of the Berkshires.
5 bedrooms, 6 beds, 2 bathrooms
12–17 Sept
4.91 out of 5 average rating, 149 reviews
Top guest favourite
Home in Savoy
Bear Minimum
2 bedrooms, 2 queen beds, 2.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 88 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
9–14 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Cabin in Hinsdale
Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
3 bedrooms, 4 beds, 1 bathroom
10–15 Sept
4.93 out of 5 average rating, 139 reviews
Guest favourite
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.96 out of 5 average rating, 50 reviews
Superhost
Home in Plainfield
A Quaint country charm - Private house at RV camp
2 bedrooms, 5 beds, 1 bathroom
19–24 Sept
4.89 out of 5 average rating, 9 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
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
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 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
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 311 reviews
Home in Pittsfield
Cozy escape to the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews