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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 15 – 20
5.0 out of 5 average rating, 26 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
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Home in Lanesborough
Historic Stone Church in The Berkshires
1 bedroom, 1 bed, 1.5 baths
Sep 20 – 25
4.96 out of 5 average rating, 90 reviews
Guest favorite
Cottage in Lanesborough
Lakefront Cottage | Private Dock, Kayaks & Firepit
2 bedrooms, 6 beds, 1 bath
Oct 5 – 10
4.79 out of 5 average rating, 14 reviews
Guest favorite
Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds, 4.5 baths
Oct 19 – 24
4.96 out of 5 average rating, 111 reviews
Top guest favorite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 baths
Sep 14 – 19
5.0 out of 5 average rating, 5 reviews
Top guest favorite
Home in Lanesborough
Berkshires Home-Near Williams College
3 bedrooms, 3 beds, 2.5 baths
Sep 20 – 25
5.0 out of 5 average rating, 31 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, 85 reviews
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Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds, 3 baths
Sep 14 – 19
5.0 out of 5 average rating, 43 reviews
Top guest favorite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 baths
Sep 14 – 19
4.97 out of 5 average rating, 78 reviews
Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds, 3 baths
Sep 15 – 20
5.0 out of 5 average rating, 4 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
Top guest favorite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 baths
Oct 14 – 19
5.0 out of 5 average rating, 20 reviews
Guest favorite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
4 bedrooms, 5 beds, 1.5 baths
Sep 14 – 19
4.97 out of 5 average rating, 79 reviews
Guest favorite
Townhouse in Hancock
Beautiful Jiminy Peak Townhome Family Friendly
3 bedrooms, 5 beds, 2 baths
Sep 16 – 21
4.83 out of 5 average rating, 109 reviews
Guest favorite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 baths
Sep 14 – 19
5.0 out of 5 average rating, 26 reviews
Guest favorite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 baths
Sep 27 – Oct 2
5.0 out of 5 average rating, 15 reviews
Top guest favorite
Home in Hancock
Grand 6BR Home by Jiminy | Hike • Hot Tub • Games
6 bedrooms, 14 beds, 5.5 baths
Sep 27 – Oct 2
4.97 out of 5 average rating, 64 reviews