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Search results; Over 1,000 homes in Lanesborough

Guest favorite
Home in Lanesborough
Elmwood Farmhouse
4 bedrooms, 7 beds, 2.5 private baths
Sep 22 – 27
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4.9 out of 5 average rating, 124 reviews
Top guest favorite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 baths
Sep 8 – 13
5.0 out of 5 average rating, 26 reviews
Top guest favorite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds, 3 baths
Sep 14 – 19
5.0 out of 5 average rating, 42 reviews
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Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bath
Nov 20 – 25
4.96 out of 5 average rating, 55 reviews
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 baths
Sep 6 – 11
5.0 out of 5 average rating, 3 reviews
Guest favorite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds, 2.5 baths
Oct 31 – Nov 5
4.85 out of 5 average rating, 300 reviews
Guest favorite
Home in Lanesborough
Historic Stone Church in The Berkshires
1 bedroom, 1 bed, 1.5 baths
Sep 6 – 11
4.98 out of 5 average rating, 88 reviews
Top guest favorite
Home in Lanesborough
Berkshires Home-Near Williams College
3 bedrooms, 3 beds, 2.5 baths
Sep 7 – 12
5.0 out of 5 average rating, 30 reviews
Guest favorite
Cottage in Lanesborough
Lakefront Cottage | Private Dock, Kayaks & Firepit
2 bedrooms, 6 beds, 1 bath
Sep 14 – 19
4.77 out of 5 average rating, 13 reviews
Top guest favorite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 baths
Sep 12 – 17
4.97 out of 5 average rating, 76 reviews
Top guest favorite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 baths
Sep 8 – 13
5.0 out of 5 average rating, 45 reviews
Guest favorite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
4 bedrooms, 5 beds, 1.5 baths
Sep 6 – 11
4.97 out of 5 average rating, 78 reviews
Top guest favorite
Apartment in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bath
Sep 6 – 11
4.92 out of 5 average rating, 328 reviews
Top guest favorite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds, 4.5 baths
Sep 26 – Oct 1
4.98 out of 5 average rating, 83 reviews
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Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 baths
Sep 5 – 10
5.0 out of 5 average rating, 20 reviews
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Apartment in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bath
Sep 7 – 12
4.97 out of 5 average rating, 129 reviews
Top guest favorite
Cabin in Lanesborough
Glamping- the Berkshires Hike on site! Car charger
3 bedrooms, 8 beds, 2 baths
Jan 7 – 12
4.98 out of 5 average rating, 55 reviews
Guest favorite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 baths
Sep 14 – 19
5.0 out of 5 average rating, 15 reviews
Top guest favorite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds, 2 baths
Sep 9 – 14
4.95 out of 5 average rating, 75 reviews