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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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Top guest favorite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 baths
Sep 1 – 6
4.94 out of 5 average rating, 47 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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Home in Pittsfield
Lake House Onota Lake
3 bedrooms, 6 beds, 2 baths
Sep 4 – 9
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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
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds, 4.5 baths
Sep 1 – 6
4.96 out of 5 average rating, 111 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 Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds, 3 baths
Sep 1 – 6
5.0 out of 5 average rating, 4 reviews
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Superhost
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bath
Sep 6 – 11
4.8 out of 5 average rating, 98 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, 73 reviews
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Superhost
Home in Pittsfield
Grand Berkshire Manor By Evergreen Home
5 bedrooms, 8 beds, 4 baths
Sep 2 – 7
New place to stay
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Superhost
Apartment in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bath
Sep 6 – 11
4.92 out of 5 average rating, 327 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
Apartment in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bath
Sep 7 – 12
4.97 out of 5 average rating, 128 reviews
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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, 19 reviews
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Top guest favorite
Cottage in Pittsfield
Charming Lakeview Cottage in the Berkshires
1 bedroom, 2 beds, 1 bath
Sep 9 – 14
5.0 out of 5 average rating, 15 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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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, 87 reviews
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Guest favorite
Home in Hancock
Family Lodge at Jiminy Peak - Pools & Adventure
4 bedrooms, 9 beds, 3 baths
Sep 1 – 6
4.95 out of 5 average rating, 58 reviews