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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
19–24 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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Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms, 4 beds, 1 bathroom
19–24 Sept
4.8 out of 5 average rating, 41 reviews
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Superhost
Cabin in Plainfield
Camp on Windsor Pond Berkshires
2 bedrooms, 2 beds, 1 bathroom
19–24 Sept
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
19–24 Sept
4.89 out of 5 average rating, 18 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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Top guest favourite
Home in Hinsdale
Modern Lakehouse with Private Lake Access
3 bedrooms, 4 beds, 2 bathrooms
19–24 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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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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Guest favourite
Flat in Hinsdale
Lakeside Getaway
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 32 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
20–25 Sept
4.93 out of 5 average rating, 140 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 Hawley
Stump Sprouts Lodge
7 bedrooms, 18 beds, 3.5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 46 reviews
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Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
21–26 Oct
4.98 out of 5 average rating, 469 reviews
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Guest house in Florida
Adorable 1 bedroom guesthouse in country setting.
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.76 out of 5 average rating, 50 reviews
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Guest favourite
Cabin in Cummington
Berkshire A-Frame Cabin!
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
4.85 out of 5 average rating, 133 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, 46 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