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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
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms, 4 beds
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
7–12 Sept
4.89 out of 5 average rating, 18 reviews
Superhost
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds
13–18 Sept
4.7 out of 5 average rating, 100 reviews
Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds
7–12 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds
21–26 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds
13–18 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Hinsdale
Modern Lakehouse with Private Lake Access
3 bedrooms, 4 beds
9–14 Sept
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Guest house in North Adams
Netherwood - North Adams Guest House with Views
3 bedrooms, 3 king beds
1–6 Nov
5.0 out of 5 average rating, 336 reviews
Top guest favourite
Home in Hinsdale
Hummingbird Haven
5 bedrooms, 6 beds
2–7 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds
14–19 Sept
5.0 out of 5 average rating, 42 reviews
Superhost
Cabin in Plainfield
Camp on Windsor Pond Berkshires
2 bedrooms, 2 beds
13–18 Sept
4.55 out of 5 average rating, 38 reviews
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds
9–14 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms, 5 beds
5–10 Oct
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms, 5 beds
20–25 Sept
4.93 out of 5 average rating, 311 reviews
Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
3 bedrooms, 5 beds
7–12 Sept
4.81 out of 5 average rating, 165 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds
5–10 Oct
4.99 out of 5 average rating, 221 reviews