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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, 296 reviews
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms, 2 beds, 1 bathroom
8–13 Jul
5.0 out of 5 average rating, 4 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
19–24 Jul
4.81 out of 5 average rating, 93 reviews
Top guest favourite
Home in Lanesborough
Historic Stone Church in The Berkshires
1 bedroom, 1 bed, 1.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 81 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, 50 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 314 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
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 11 reviews
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds, 1 bathroom
25–30 Jul
4.82 out of 5 average rating, 207 reviews
Guest favourite
Cottage in Lanesborough
Stone School Cottage
2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
4.93 out of 5 average rating, 258 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
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5 bedrooms, 4.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 35 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 316 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 457 reviews
Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bedroom, 1 bed, 1 bathroom
9–14 Jul
4.9 out of 5 average rating, 174 reviews
Flat in Pittsfield
Spacious Green 2 bedroom Downtown
2 bedrooms, 4 beds, 1 bathroom
26–31 Jul
4.82 out of 5 average rating, 49 reviews
Home in Lanesborough
Casa Demeo, Private Berkshire Retreat
3 bedrooms, 3 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Apartment in Hancock
THE SLOPE slope-view Country Inn 1BR w/heated pool
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 5 reviews