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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
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
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 baths
Sep 7 – 12
5.0 out of 5 average rating, 4 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
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
Guest favorite
Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds, 4.5 baths
Sep 28 – Oct 3
4.96 out of 5 average rating, 111 reviews
Guest favorite
Home in Lanesborough
Historic Stone Church in The Berkshires
1 bedroom, 1 bed, 1.5 baths
Sep 13 – 18
4.98 out of 5 average rating, 89 reviews
Top guest favorite
Home in Lanesborough
Berkshires Home-Near Williams College
3 bedrooms, 3 beds, 2.5 baths
Sep 9 – 14
5.0 out of 5 average rating, 30 reviews
Guest favorite
Home in Hancock
Family Lodge at Jiminy Peak - Pools & Adventure
4 bedrooms, 9 beds, 3 baths
Sep 7 – 12
4.93 out of 5 average rating, 59 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
Superhost
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bath
Sep 12 – 17
4.78 out of 5 average rating, 101 reviews
Guest favorite
Townhouse in Hancock
Beautiful Jiminy Peak Townhome Family Friendly
3 bedrooms, 5 beds, 2 baths
Sep 9 – 14
4.83 out of 5 average rating, 109 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
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
Guest favorite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds, 1 bath
Sep 8 – 13
4.82 out of 5 average rating, 213 reviews
Guest favorite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 baths
Sep 9 – 14
5.0 out of 5 average rating, 25 reviews
Top guest favorite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 baths
Sep 9 – 14
5.0 out of 5 average rating, 45 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