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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
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
Top guest favorite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
3 bedrooms, 4 beds, 2.5 baths
Sep 7 – 12
4.99 out of 5 average rating, 135 reviews
Guest favorite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bath
Sep 9 – 14
4.97 out of 5 average rating, 75 reviews
Superhost
Home in Pittsfield
Grand Berkshire Manor By Evergreen Home
5 bedrooms, 8 beds, 4 baths
Sep 7 – 12
New place to stay
Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds, 3 baths
Sep 6 – 11
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 baths
Sep 8 – 13
4.95 out of 5 average rating, 42 reviews
Top guest favorite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 baths
Sep 7 – 12
4.94 out of 5 average rating, 47 reviews
Top guest favorite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
4 bedrooms, 4 beds, 2.5 baths
Sep 7 – 12
4.97 out of 5 average rating, 59 reviews
Top guest favorite
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
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
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
Home in Pittsfield
house w/ view in the Berkshires.
3 bedrooms, 9 beds, 2 baths
Sep 8 – 13
4.8 out of 5 average rating, 10 reviews
Top guest favorite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bath
Nov 20 – 25
4.96 out of 5 average rating, 55 reviews
Top guest favorite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds, 2.5 baths
Sep 12 – 17
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
2 bedrooms, 2 beds, 1 bath
Sep 21 – 26
4.88 out of 5 average rating, 32 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