filters

Search results; Over 1,000 homes in Windsor

Photo 1 of 29
Guest favourite
Home in Windsor
Beautiful Log Cabin with a Mountain View
3 bedrooms, 3 beds, 1 shared bathroom
17–22 Feb
,
5.0 out of 5 average rating, 7 reviews
Photo 1 of 29
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
Photo 1 of 29
Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms, 4 beds, 1 bathroom
18–23 Sept
4.8 out of 5 average rating, 41 reviews
Photo 1 of 29
Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
4.89 out of 5 average rating, 18 reviews
Photo 1 of 21
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
Photo 1 of 26
Guest favourite
Cabin in Windsor
Stone cabin in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
18–23 Sept
4.88 out of 5 average rating, 32 reviews
Photo 1 of 29
Top guest favourite
Home in Hinsdale
Modern Lakehouse with Private Lake Access
3 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
4.97 out of 5 average rating, 31 reviews
Photo 1 of 29
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
Photo 1 of 24
Superhost
Cabin in Plainfield
Camp on Windsor Pond Berkshires
2 bedrooms, 2 beds, 1 bathroom
18–23 Sept
4.56 out of 5 average rating, 39 reviews
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Home in Adams
Beautiful Victorian. The heart of the Berkshires.
5 bedrooms, 6 beds, 2 bathrooms
18–23 Sept
4.91 out of 5 average rating, 149 reviews
Photo 1 of 29
Guest favourite
Cabin in Hinsdale
Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
3 bedrooms, 4 beds, 1 bathroom
18–23 Sept
4.93 out of 5 average rating, 140 reviews
Photo 1 of 27
Guest favourite
Home in Savoy
Bear Minimum
2 bedrooms, 2 queen beds, 2.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 89 reviews
Photo 1 of 29
Top guest favourite
Home in North Adams
Steps to MoCA private house + SAUNA!
4 bedrooms, 6 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 560 reviews
Photo 1 of 29
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
Photo 1 of 29
Guest favourite
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
2 bedrooms, 3 beds, 1 bathroom
18–23 Sept
4.96 out of 5 average rating, 50 reviews
Photo 1 of 17
Guest favourite
Flat in Dalton
1843 House - Bright and Airy 5 Rooms (2 Bedrooms)
2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
4.91 out of 5 average rating, 22 reviews
Photo 1 of 29
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
Photo 1 of 29
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, 9 reviews