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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
Guest favorite
Cottage in Pittsfield
Lake Views & Dock Access - Pittsfield Cottage!
4 bedrooms, 6 beds, 1.5 baths
Sep 15 – 20
5.0 out of 5 average rating, 9 reviews
Home in Pittsfield
house w/ view in the Berkshires.
3 bedrooms, 9 beds, 2 baths
Sep 18 – 23
4.82 out of 5 average rating, 11 reviews
Guest favorite
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
Top guest favorite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 baths
Sep 16 – 21
5.0 out of 5 average rating, 26 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 15 – 20
4.79 out of 5 average rating, 103 reviews
Top guest favorite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 baths
Sep 19 – 24
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bath
Sep 15 – 20
4.96 out of 5 average rating, 76 reviews
Top guest favorite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
4 bedrooms, 4 beds, 2.5 baths
Sep 15 – 20
4.97 out of 5 average rating, 60 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
Top guest favorite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 baths
Oct 4 – 9
4.95 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 15 – 20
4.97 out of 5 average rating, 78 reviews
Guest favorite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
2 bedrooms, 2 beds, 1 bath
Sep 26 – Oct 1
4.88 out of 5 average rating, 33 reviews
Top guest favorite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 baths
Sep 20 – 25
4.94 out of 5 average rating, 47 reviews
Guest favorite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 baths
Sep 15 – 20
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 15 – 20
5.0 out of 5 average rating, 43 reviews
Guest favorite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds, 1 bath
Oct 28 – Nov 2
4.93 out of 5 average rating, 135 reviews
Guest favorite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
4 bedrooms, 5 beds, 1.5 baths
Sep 16 – 21
4.97 out of 5 average rating, 79 reviews
Guest favorite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
7 bedrooms, 8 beds, 4.5 baths
Sep 20 – 25
4.78 out of 5 average rating, 113 reviews