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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, 123 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
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
Home in Pittsfield
Cozy lake Cottage
2 bedrooms, 2 beds, 1.5 baths
Sep 6 – 11
New place to stay
Superhost
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bath
Sep 5 – 10
4.79 out of 5 average rating, 97 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, 299 reviews
Guest favorite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bath
Sep 2 – 7
4.97 out of 5 average rating, 73 reviews
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, 77 reviews
Home in Pittsfield
Lake House Onota Lake
3 bedrooms, 6 beds, 2 baths
Sep 1 – 6
Guest favorite
Cottage in Lanesborough
Stone School Cottage
2 bedrooms, 4 beds, 1 bath
Sep 13 – 18
4.93 out of 5 average rating, 264 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bath
Sep 6 – 11
4.92 out of 5 average rating, 326 reviews
Top guest favorite
Home in Lanesborough
Berkshires Home-Near Williams College
3 bedrooms, 3 beds, 2.5 baths
Sep 7 – 12
5.0 out of 5 average rating, 30 reviews
Top guest favorite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 baths
Sep 1 – 6
4.95 out of 5 average rating, 40 reviews
Home in Pittsfield
3 Bed Home Lake & Mountain Views
3 bedrooms, 3 beds, 2 baths
Sep 7 – 12
4.71 out of 5 average rating, 14 reviews
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
Guest favorite
Home in Pittsfield
Friendly Hills | Passive Home • EV Charger
3 bedrooms, 4 beds, 2 baths
Sep 14 – 19
4.91 out of 5 average rating, 43 reviews
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
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
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, 54 reviews