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Search results; Over 1,000 homes in Windsor

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Guest favourite
Cabin in Windsor
Stone cabin in the Berkshires
2 bedrooms, 3 beds, 1 private bathroom
1–6 Sept
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4.87 out of 5 average rating, 31 reviews
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Superhost
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.69 out of 5 average rating, 98 reviews
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Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
4.88 out of 5 average rating, 17 reviews
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Guest favourite
Home in Windsor
Beautiful Log Cabin with a Mountain View
3 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 7 reviews
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Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms, 4 beds, 1 bathroom
1–6 Sept
4.8 out of 5 average rating, 41 reviews
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Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 49 reviews
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Guest favourite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
7 bedrooms, 8 beds, 4.5 bathrooms
20–25 Sept
4.78 out of 5 average rating, 113 reviews
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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, 148 reviews
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Top guest favourite
Home in North Adams
Steps to MoCA private house + SAUNA!
4 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 552 reviews
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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
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Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
4.81 out of 5 average rating, 165 reviews
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Top guest favourite
Home in Adams
Relaxing Berkshires Home With a View!
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Guest house in North Adams
Netherwood - North Adams Guest House with Views
3 bedrooms, 3 king beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 335 reviews
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Top guest favourite
Home in Hinsdale
Hummingbird Haven
5 bedrooms, 6 beds, 3.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 74 reviews
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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
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Guest favourite
Home in Adams
Spacious Home by Mt. Greylock
4 bedrooms, 5 beds, 3 bathrooms
4–9 Sept
4.91 out of 5 average rating, 54 reviews
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Top guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
5 bedrooms, 7 beds, 2.5 bathrooms
9–14 Sept
4.93 out of 5 average rating, 210 reviews