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Search results; Over 1,000 homes in Hinsdale

Top guest favourite
Cottage in Hinsdale
Cozy Cottage in the Berkshires
2 bedrooms, 3 beds, 1 private bathroom
27 Oct – 1 Nov
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4.99 out of 5 average rating, 169 reviews
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
Guest favourite
Cabin in Hinsdale
Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
3 bedrooms, 4 beds, 1 bathroom
15–20 Sept
4.93 out of 5 average rating, 140 reviews
Top guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 50 reviews
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
Top guest favourite
Home in Hinsdale
Berkshire Cabin by Lake Ashmere
3 bedrooms, 3 beds, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Hinsdale
Modern Lake Cottage - 3 minute walk to beach
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Hinsdale
Private Beach on Ashmere Lake (In the Berkshires)
3 bedrooms, 6 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Hinsdale
Modern Lakehouse with Private Lake Access
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Hinsdale
Berkshire Lake Retreat
4 bedrooms, 4 beds, 2 bathrooms
25–30 Sept
4.9 out of 5 average rating, 72 reviews
Guest favourite
Home in Pittsfield
The Reel Retreat | Theatre & Firepit • Game Room
4 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 19 reviews
Cottage in Hinsdale
Berkshire Cottage - Relaxation Destination
3 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.62 out of 5 average rating, 74 reviews
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
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
4.95 out of 5 average rating, 75 reviews
Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
5 bedrooms, 7 beds, 2.5 bathrooms
22–27 Sept
4.93 out of 5 average rating, 212 reviews
Guest favourite
Home in Pittsfield
Berkshire Views
6 bedrooms, 7 beds, 4 bathrooms
11–16 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 76 reviews