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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
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.8 out of 5 average rating, 92 reviews
Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
3 bedrooms, 3 beds, 1 bathroom
22–27 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Home in Lanesborough
Historic Stone Church in The Berkshires
1 bedroom, 1 bed, 1.5 bathrooms
5–10 Jul
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 41 reviews
Guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 122 reviews
Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
4.85 out of 5 average rating, 295 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, 23 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Nov
4.97 out of 5 average rating, 67 reviews
Guest favourite
Cottage in Pittsfield
Lake Views & Dock Access - Pittsfield Cottage!
4 bedrooms, 6 beds, 1.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds, 4.5 bathrooms
1–6 Sept
4.96 out of 5 average rating, 109 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in Lanesborough
Lake, Berkshire Fave, Hot Tub, Lg Open LR, Family
4 bedrooms, 10 beds, 2 bathrooms
24–29 Aug
4.99 out of 5 average rating, 71 reviews
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
4.93 out of 5 average rating, 104 reviews
Guest favourite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
2 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
4.92 out of 5 average rating, 104 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Cottage in Lanesborough
The Grove Lakehouse
2 bedrooms, 6 beds, 1 bathroom
27 Jul – 1 Aug
4.86 out of 5 average rating, 7 reviews