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Search results; Over 1,000 homes in Lanesborough

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Top guest favourite
Cottage in Lanesborough
Pontoosuc Lakeshore
2 bedrooms, 3 beds, 1.5 private bathrooms
1–6 Jan
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4.97 out of 5 average rating, 31 reviews
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Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 26 reviews
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Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds
14–19 Sept
5.0 out of 5 average rating, 42 reviews
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Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds
1–6 Sept
4.96 out of 5 average rating, 111 reviews
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Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds
31 Oct – 5 Nov
4.85 out of 5 average rating, 300 reviews
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Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds
7–12 Sept
4.94 out of 5 average rating, 47 reviews
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Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds
6–11 Sept
New place to stay
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Home in Lanesborough
The Pond House
3 bedrooms, 4 beds
20–25 Nov
4.96 out of 5 average rating, 55 reviews
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Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds
1–6 Sept
5.0 out of 5 average rating, 20 reviews
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Home in Hancock
Family Lodge at Jiminy Peak - Pools & Adventure
4 bedrooms, 9 beds
7–12 Sept
4.95 out of 5 average rating, 58 reviews
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Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 83 reviews
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Home in Lanesborough
Berkshires Home-Near Williams College
3 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 30 reviews
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Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds
6–11 Sept
4.97 out of 5 average rating, 74 reviews
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Home in Lanesborough
Historic Stone Church in The Berkshires
1 bedroom, 1 bed
6–11 Sept
4.98 out of 5 average rating, 88 reviews
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Home in Lanesborough
Mountain Blossom Retreat by Evergreen Home
3 bedrooms, 4 beds
21–26 Sept
5.0 out of 5 average rating, 41 reviews
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Home in Lanesborough
Elmwood Farmhouse
4 bedrooms, 7 beds
22–27 Sept
4.9 out of 5 average rating, 124 reviews
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Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 44 reviews
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Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds
7–12 Sept
4.97 out of 5 average rating, 128 reviews
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Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds
1–6 Sept
4.95 out of 5 average rating, 75 reviews