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Search results; Over 1,000 homes in Lanesborough

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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
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Guest favorite
Cottage in Pittsfield
Lake Views & Dock Access - Pittsfield Cottage!
4 bedrooms, 6 beds, 1.5 baths
Sep 7 – 12
5.0 out of 5 average rating, 9 reviews
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Guest favorite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
4 bedrooms, 5 beds, 1.5 baths
Sep 1 – 6
4.97 out of 5 average rating, 78 reviews
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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
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Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 baths
Sep 6 – 11
New place to stay
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Top guest favorite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 baths
Sep 3 – 8
4.94 out of 5 average rating, 47 reviews
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Home in Pittsfield
Grand Berkshire Manor By Evergreen Home
5 bedrooms, 8 beds, 4 baths
Sep 3 – 8
New place to stay
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Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds, 3 baths
Sep 2 – 7
5.0 out of 5 average rating, 4 reviews
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Top guest favorite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 baths
Sep 1 – 6
5.0 out of 5 average rating, 20 reviews
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Top guest favorite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds, 2 baths
Sep 3 – 8
4.95 out of 5 average rating, 75 reviews
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Home in Pittsfield
Lake House Onota Lake
3 bedrooms, 6 beds, 2 baths
Sep 8 – 13
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Guest favorite
Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds, 4.5 baths
Sep 3 – 8
4.96 out of 5 average rating, 111 reviews
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Guest favorite
Cottage in Lanesborough
Lakefront Cottage | Private Dock, Kayaks & Firepit
2 bedrooms, 6 beds, 1 bath
Sep 8 – 13
4.77 out of 5 average rating, 13 reviews
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Guest favorite
Home in Lanesborough
Mountain Serenity 20 Acres, Hot Tub, Jiminy<10min
4 bedrooms, 5 beds, 2 baths
Sep 2 – 7
4.98 out of 5 average rating, 40 reviews
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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, 75 reviews
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Home in Pittsfield
3 Bed Home Lake & Mountain Views
3 bedrooms, 3 beds, 2 baths
Sep 7 – 12
4.73 out of 5 average rating, 15 reviews
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Top guest favorite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds, 2.5 baths
Sep 8 – 13
5.0 out of 5 average rating, 14 reviews
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Top guest favorite
Home in Lanesborough
Mountain Blossom Retreat by Evergreen Home
3 bedrooms, 4 beds, 3.5 baths
Sep 21 – 26
5.0 out of 5 average rating, 41 reviews
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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, 74 reviews