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Search results; Over 1,000 homes in Lanesborough

Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds, 2.5 private bathrooms
9–14 Aug
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4.85 out of 5 average rating, 295 reviews
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 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
5–10 Jul
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
Guest favourite
Cottage in Lanesborough
The Grove Lakehouse
4.86 out of 5 average rating, 7 reviews, 2 bedrooms, 6 beds, 1 bathroom
27 Jul – 1 Aug
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
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 14 reviews, 2 beds, 3 bathrooms
12–17 Jul
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
Home in Pittsfield
Brady’s Croft | Berkshires Farmhouse Retreat
New place to stay, 5 bedrooms, 6 beds, 3 bathrooms
5–10 Jul
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
Cabin in Cheshire
Private Paradise in the Berkshires
4.9 out of 5 average rating, 173 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Jul
Guest favourite
Cottage in Lanesborough
Stone School Cottage
4.93 out of 5 average rating, 258 reviews, 2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds, 3 bathrooms
7–12 Jul
Guest favourite
Apartment in Hancock
THE SLOPE slope-view Country Inn 1BR w/heated pool
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
4.82 out of 5 average rating, 207 reviews, 2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
4.97 out of 5 average rating, 115 reviews, 3 bedrooms, 3 beds, 1 bathroom
4–9 Jul
Guest favourite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
4.8 out of 5 average rating, 49 reviews, 3 bedrooms, 4 beds, 1 bathroom
18–23 Jul
Top guest favourite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
4.99 out of 5 average rating, 132 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug