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Search results; Over 1,000 homes in Windsor

Guest favourite
Cabin in Windsor
Stone cabin in the Berkshires
2 bedrooms, 3 beds, 1 private bathroom
12–17 Sept
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4.88 out of 5 average rating, 32 reviews
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
Guest favourite
Home in Windsor
Beautiful Log Cabin with a Mountain View
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 7 reviews
Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.8 out of 5 average rating, 41 reviews
Superhost
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.7 out of 5 average rating, 99 reviews
Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms, 5 beds, 3 bathrooms
5–10 Sept
4.88 out of 5 average rating, 17 reviews
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
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, 211 reviews
Room in Cummington
Singing Bridge Turquoise Room (single room)
1 queen bed, 1 bathroom
8–13 Sept
4.72 out of 5 average rating, 95 reviews
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
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
Top guest favourite
Flat in Plainfield
Sunny carriage house apartment
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
4.95 out of 5 average rating, 304 reviews
Top guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 8 reviews
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
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, 175 reviews
Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
5–10 Sept
5.0 out of 5 average rating, 20 reviews
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
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Hinsdale
Modern Lake Cottage - 3 minute walk to beach
2 bedrooms, 2 king beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 7 reviews