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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
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Jul
Guest favourite
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
4.81 out of 5 average rating, 93 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
5.0 out of 5 average rating, 41 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Jul
Top guest favourite
Guest house in Lanesborough
The Carriage House: Spotless, Charming 2 Bedroom
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
Guest favourite
Home in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
4.91 out of 5 average rating, 46 reviews, 3 bedrooms, 3 beds, 1 bathroom
22–27 Sept
Guest favourite
Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
4.96 out of 5 average rating, 109 reviews, 6 bedrooms, 10 beds, 4.5 bathrooms
1–6 Sept
Guest favourite
Cottage in Pittsfield
Lake Views & Dock Access - Pittsfield Cottage!
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 6 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Home in Lanesborough
Historic Stone Church in The Berkshires
4.98 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
2–7 Aug
Home in Lanesborough
Casa Demeo, Private Berkshire Retreat
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 3 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Lanesborough
The Pond House
4.96 out of 5 average rating, 49 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
5.0 out of 5 average rating, 23 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
4.97 out of 5 average rating, 67 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Nov
Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
4.85 out of 5 average rating, 296 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
Guest favourite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
4.92 out of 5 average rating, 104 reviews, 2 bedrooms, 3 beds, 2 bathrooms
18–23 Jul
Guest favourite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
4.82 out of 5 average rating, 22 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 83 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
4.93 out of 5 average rating, 104 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
4.94 out of 5 average rating, 35 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul