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Search results; Over 1,000 homes in Lanesborough

Top guest favourite
Cabin in Lanesborough
Glamping- the Berkshires Hike on site! Car charger
3 bedrooms, 8 beds, 2 private bathrooms
7–12 Jan
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4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 bathrooms
5–10 Sept
4.94 out of 5 average rating, 47 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
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
Top guest favourite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds, 2.5 bathrooms
10–15 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
5–10 Sept
New place to stay
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
6–11 Sept
New place to stay
Guest favourite
Home in Lanesborough
Mountain Serenity 20 Acres, Hot Tub, Jiminy<10min
4 bedrooms, 5 beds, 2 bathrooms
4–9 Sept
4.98 out of 5 average rating, 40 reviews
Guest favourite
Cottage in Lanesborough
Lakefront Cottage | Private Dock, Kayaks & Firepit
2 bedrooms, 6 beds, 1 bathroom
14–19 Sept
4.77 out of 5 average rating, 13 reviews
Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
3–8 Sept
5.0 out of 5 average rating, 20 reviews
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, 41 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
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 74 reviews
Guest favourite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
7 bedrooms, 8 beds, 4.5 bathrooms
20–25 Sept
4.78 out of 5 average rating, 113 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
4.96 out of 5 average rating, 55 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 45 reviews
Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds, 3 bathrooms
4–9 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cabin in Pittsfield
Summer Cottage in the Berkshires
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 114 reviews