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Search results; Over 1,000 homes in Lanesborough

Top guest favourite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds, 3 private bathrooms
14–19 Sept
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5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 26 reviews
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds, 2.5 bathrooms
31 Oct – 5 Nov
4.85 out of 5 average rating, 300 reviews
Guest favourite
Home in Lanesborough
Elmwood Farmhouse
4 bedrooms, 7 beds, 2.5 bathrooms
22–27 Sept
4.9 out of 5 average rating, 124 reviews
Top guest favourite
Home in Lanesborough
Berkshires Home-Near Williams College
3 bedrooms, 3 beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds, 4.5 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 111 reviews
Guest favourite
Cottage in Lanesborough
Lakefront Cottage | Private Dock, Kayaks & Firepit
2 bedrooms, 6 beds, 1 bathroom
14–19 Sept
4.77 out of 5 average rating, 13 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 76 reviews
Guest favourite
Home in Lanesborough
Historic Stone Church in The Berkshires
1 bedroom, 1 bed, 1.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 89 reviews
Guest favourite
Home in Lanesborough
Mountain Blossom Retreat by Evergreen Home
3 bedrooms, 4 beds, 3.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
4 bedrooms, 5 beds, 1.5 bathrooms
8–13 Sept
4.97 out of 5 average rating, 78 reviews
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
4.95 out of 5 average rating, 75 reviews
Top guest favourite
Home in Hancock
Grand 6BR Home by Jiminy | Hike • Hot Tub • Games
6 bedrooms, 14 beds, 5.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds, 4.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 84 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.95 out of 5 average rating, 234 reviews
Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 20 reviews