filters

Search results; Over 1,000 homes in Lanesborough

Photo 1 of 29
Guest favorite
Home in Lanesborough
Elmwood Farmhouse
4 bedrooms, 7 beds, 2.5 private baths
Oct 20 – 25
,
4.9 out of 5 average rating, 124 reviews
Photo 1 of 18
Guest favorite
Home in Lanesborough
Historic Stone Church in The Berkshires
1 bedroom, 1 bed
Oct 4 – 9
4.96 out of 5 average rating, 90 reviews
Photo 1 of 29
Guest favorite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds
Nov 8 – 13
4.85 out of 5 average rating, 300 reviews
Photo 1 of 29
Top guest favorite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds
Oct 1 – 6
5.0 out of 5 average rating, 43 reviews
Photo 1 of 29
Top guest favorite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds
Oct 1 – 6
5.0 out of 5 average rating, 26 reviews
Photo 1 of 22
Top guest favorite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds
Oct 1 – 6
4.94 out of 5 average rating, 47 reviews
Photo 1 of 29
Top guest favorite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds
Oct 18 – 23
5.0 out of 5 average rating, 7 reviews
Photo 1 of 9
Superhost
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds
Oct 1 – 6
4.79 out of 5 average rating, 103 reviews
Photo 1 of 29
Guest favorite
Townhouse in Hancock
Beautiful Jiminy Peak Townhome Family Friendly
3 bedrooms, 5 beds
Oct 1 – 6
4.83 out of 5 average rating, 109 reviews
Photo 1 of 29
Top guest favorite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds
Oct 3 – 8
4.97 out of 5 average rating, 78 reviews
Photo 1 of 29
Guest favorite
Cottage in Lanesborough
Lakefront Cottage | Private Dock, Kayaks & Firepit
2 bedrooms, 6 beds
Oct 25 – 30
4.79 out of 5 average rating, 14 reviews
Photo 1 of 29
Guest favorite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds
Oct 1 – 6
5.0 out of 5 average rating, 15 reviews
Photo 1 of 29
Top guest favorite
Apartment in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds
Oct 4 – 9
4.97 out of 5 average rating, 130 reviews
Photo 1 of 29
Top guest favorite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds
Oct 4 – 9
4.98 out of 5 average rating, 85 reviews
Photo 1 of 29
Guest favorite
Cottage in Pittsfield
Lake Views & Dock Access - Pittsfield Cottage!
4 bedrooms, 6 beds
Oct 1 – 6
5.0 out of 5 average rating, 9 reviews
Photo 1 of 29
Top guest favorite
Apartment in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
Oct 22 – 27
4.92 out of 5 average rating, 330 reviews
Photo 1 of 29
Top guest favorite
Guesthouse in Lanesborough
The Carriage House: Spotless, Charming 2 Bedroom
2 bedrooms, 2 beds
Oct 29 – Nov 3
5.0 out of 5 average rating, 20 reviews
Photo 1 of 15
Top guest favorite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds
Oct 13 – 18
4.95 out of 5 average rating, 75 reviews
Photo 1 of 29
Superhost
Home in Hancock
Comfortable Berkshires retreat on mtn resort, SISO
4 bedrooms, 12 beds
Oct 1 – 6
4.84 out of 5 average rating, 58 reviews