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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 Jan
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4.88 out of 5 average rating, 32 reviews
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Guest favourite
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.71 out of 5 average rating, 102 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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Superhost
Cabin in Plainfield
Camp on Windsor Pond Berkshires
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.58 out of 5 average rating, 40 reviews
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Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
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
1–6 Oct
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
3–8 Nov
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms, 5 beds, 2 bathrooms
30 Nov – 5 Dec
4.93 out of 5 average rating, 311 reviews
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Guest favourite
Home in Plainfield
A Quaint country charm - Private house at RV camp
2 bedrooms, 5 beds, 1 bathroom
23–28 Oct
4.91 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Hinsdale
Hummingbird Haven
5 bedrooms, 6 beds, 3.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Cabin in Plainfield
Peaceful Cabin in the Woods
2 bedrooms, 2 king beds, 2 bathrooms
19–24 Oct
4.92 out of 5 average rating, 258 reviews
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Superhost
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.79 out of 5 average rating, 103 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
Cabin in Hinsdale
Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
3 bedrooms, 4 beds, 1 bathroom
12–18 Oct
4.93 out of 5 average rating, 140 reviews
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Guest house in Florida
Adorable 1 bedroom guesthouse in country setting.
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.76 out of 5 average rating, 50 reviews
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Superhost
Home in Cheshire
19th c. Barn in The Berkshires
3 bedrooms, 6 beds, 2 bathrooms
18–23 Oct
4.85 out of 5 average rating, 230 reviews
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Top guest favourite
Home in Hawley
Mountain Biking Hub: 5 Mi to Berkshire East!
4 bedrooms, 4 beds, 1.5 bathrooms
1–6 Oct
4.95 out of 5 average rating, 43 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
Cabin in Cummington
Berkshire A-Frame Cabin!
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
4.85 out of 5 average rating, 133 reviews