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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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4.88 out of 5 average rating, 32 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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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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Superhost
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.7 out of 5 average rating, 99 reviews
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Top guest favourite
Cottage in Hinsdale
Cozy Cottage in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
23–28 Oct
4.99 out of 5 average rating, 168 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
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Top guest favourite
Home in Savoy
Bear Minimum
2 bedrooms, 2 queen beds, 2.5 bathrooms
7–12 Sept
4.94 out of 5 average rating, 88 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
10–15 Sept
4.93 out of 5 average rating, 139 reviews
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Top guest favourite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 311 reviews
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Room in Cummington
Singing Bridge Turquoise Room (single room)
1 queen bed, 1 bathroom
8–13 Sept
4.71 out of 5 average rating, 94 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, 20 reviews
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Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
1–6 Sept
4.98 out of 5 average rating, 266 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, 555 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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Guest favourite
Room in Dalton
Mother in Law unit in Dalton
1 king bed, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 174 reviews
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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, 59 reviews
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Superhost
Home in Plainfield
A Quaint country charm - Private house at RV camp
2 bedrooms, 5 beds, 1 bathroom
8–13 Sept
4.89 out of 5 average rating, 9 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, 50 reviews
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Guest favourite
Home in Worthington
Berkshires Carriage House - Artist's Loft, Retreat
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 44 reviews