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Search results; Over 1,000 homes in Hinsdale

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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
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Top guest favourite
Home in Hinsdale
Hummingbird Haven
5 bedrooms, 6 beds, 3.5 bathrooms
3–8 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
13–18 Oct
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
12–18 Oct
4.93 out of 5 average rating, 140 reviews
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Guest favourite
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 50 reviews
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Guest favourite
Home in Hinsdale
Berkshire Lake Retreat
4 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.9 out of 5 average rating, 72 reviews
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Guest favourite
Flat in Hinsdale
Lakeside Getaway
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 33 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, 61 reviews
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Cottage in Hinsdale
Berkshire Cottage - Relaxation Destination
3 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.62 out of 5 average rating, 74 reviews
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Guest favourite
Flat in Dalton
1843 House - Bright and Airy 5 Rooms (2 Bedrooms)
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
4.91 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
5 bedrooms, 7 beds, 2.5 bathrooms
26–31 Oct
4.93 out of 5 average rating, 212 reviews
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Top guest favourite
Home in Hinsdale
Private Beach on Ashmere Lake (In the Berkshires)
3 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
3–8 Nov
5.0 out of 5 average rating, 20 reviews
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Top 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, 8 reviews
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Guest favourite
Home in Dalton
Cleveland House - renovated Berkshires' gem.
6 bedrooms, 8 beds, 3 bathrooms
1–6 Aug
4.99 out of 5 average rating, 181 reviews
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Guest favourite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
7 bedrooms, 8 beds, 4.5 bathrooms
18–23 Oct
4.78 out of 5 average rating, 113 reviews
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Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
2–7 Oct
4.84 out of 5 average rating, 194 reviews
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Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 130 reviews
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Home in Dalton
Comfortable Charming Home in Dalton
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
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