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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
17–22 Sept
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4.88 out of 5 average rating, 32 reviews
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Guest favourite
Home in Windsor
Beautiful Log Cabin with a Mountain View
3 bedrooms, 3 beds, 1 bathroom
17–22 Feb
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.71 out of 5 average rating, 102 reviews
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Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms, 5 beds, 3 bathrooms
17–22 Sept
4.89 out of 5 average rating, 18 reviews
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Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms, 4 beds, 1 bathroom
17–22 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
14–19 Oct
5.0 out of 5 average rating, 20 reviews
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Superhost
Cabin in Plainfield
Camp on Windsor Pond Berkshires
2 bedrooms, 2 beds, 1 bathroom
17–22 Sept
4.56 out of 5 average rating, 39 reviews
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Top guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
2 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Hinsdale
Modern Lakehouse with Private Lake Access
3 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
4.97 out of 5 average rating, 31 reviews
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Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Nov
4.85 out of 5 average rating, 300 reviews
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Superhost
Home in Cheshire
19th c. Barn in The Berkshires
3 bedrooms, 6 beds, 2 bathrooms
27 Sept – 2 Oct
4.85 out of 5 average rating, 229 reviews
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Top guest favourite
Guest suite in Dalton
Berkshires getaway: nature, culture & relaxation
1 bed, 1 bathroom
17–22 Sept
4.99 out of 5 average rating, 80 reviews
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Top guest favourite
Cottage in Hinsdale
Lake Escape in the Berkshires
1 bedroom, 2 beds, 1 bathroom
26–31 May
4.92 out of 5 average rating, 60 reviews
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Guest favourite
Home in Worthington
Berkshires Carriage House - Artist's Loft, Retreat
3 bedrooms, 4 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
5 bedrooms, 7 beds, 2.5 bathrooms
26–31 Oct
4.93 out of 5 average rating, 212 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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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
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Guest favourite
Home in Ashfield
Pondside Retreat - Entire House
3 bedrooms, 5 beds, 2 bathrooms
1–6 Dec
4.88 out of 5 average rating, 16 reviews
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Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
18–23 Oct
4.98 out of 5 average rating, 268 reviews