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Search results; Over 1,000 homes in Lanesborough

Top guest favourite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds, 3 private bathrooms
14–19 Sept
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5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 bathrooms
8–13 Sept
4.94 out of 5 average rating, 47 reviews
Guest favourite
Cottage in Pittsfield
Lake Views & Dock Access - Pittsfield Cottage!
4 bedrooms, 6 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.79 out of 5 average rating, 100 reviews
Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Sept
4.96 out of 5 average rating, 76 reviews
Top guest favourite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Pittsfield
Grand Berkshire Manor By Evergreen Home
5 bedrooms, 8 beds, 4 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.99 out of 5 average rating, 135 reviews
Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Home in Pittsfield
house w/ view in the Berkshires.
3 bedrooms, 9 beds, 2 bathrooms
9–14 Sept
4.8 out of 5 average rating, 10 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 76 reviews
Top guest favourite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
4 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.97 out of 5 average rating, 59 reviews
Guest favourite
Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds, 4.5 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 111 reviews
Top guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
8–13 Sept
4.95 out of 5 average rating, 42 reviews
Guest favourite
Cottage in Lanesborough
Stone School Cottage
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 264 reviews
Home in Pittsfield
3 Bed Home Lake & Mountain Views
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.73 out of 5 average rating, 15 reviews
Guest favourite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
4.88 out of 5 average rating, 32 reviews