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Search results; Over 1,000 homes in Lanesborough

Top guest favourite
Home in Lanesborough
Berkshires Home-Near Williams College
3 bedrooms, 3 beds, 2.5 private bathrooms
20–25 Sept
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5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 26 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
Cottage in Lanesborough
Lakefront Cottage | Private Dock, Kayaks & Firepit
2 bedrooms, 6 beds, 1 bathroom
5–10 Oct
4.79 out of 5 average rating, 14 reviews
Guest favourite
Home in Lanesborough
Historic Stone Church in The Berkshires
1 bedroom, 1 bed, 1.5 bathrooms
13–18 Sept
4.96 out of 5 average rating, 90 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
Top guest favourite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds, 4.5 bathrooms
19–24 Oct
4.96 out of 5 average rating, 111 reviews
Top guest favourite
Cabin in Lanesborough
Glamping- the Berkshires Hike on site! Car charger
3 bedrooms, 8 beds, 2 bathrooms
7–12 Jan
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 46 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
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
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
Top guest favourite
Home in Lanesborough
Berkshire 6BR Estate • Pool, Hot Tub, Game Room
6 bedrooms, 9 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 58 reviews
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
Guest favourite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
4 bedrooms, 5 beds, 1.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 79 reviews
Guest favourite
Townhouse in Hancock
Beautiful Jiminy Peak Townhome Family Friendly
3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
4.83 out of 5 average rating, 109 reviews