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Search results; Over 1,000 homes in Lanesborough

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Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds, 2.5 private bathrooms
8–13 Nov
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4.85 out of 5 average rating, 300 reviews
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Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 26 reviews
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Guest favourite
Home in Lanesborough
Elmwood Farmhouse
4 bedrooms, 7 beds, 2.5 bathrooms
20–25 Oct
4.9 out of 5 average rating, 124 reviews
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Top guest favourite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds, 4.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 85 reviews
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Top guest favourite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 43 reviews
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Guest favourite
Home in Lanesborough
Historic Stone Church in The Berkshires
1 bedroom, 1 bed, 1.5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 90 reviews
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Top guest favourite
Home in Lanesborough
Berkshires Home-Near Williams College
3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 31 reviews
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Top guest favourite
Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Lanesborough
Berkshire 6BR Estate • Pool, Hot Tub, Game Room
6 bedrooms, 9 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 58 reviews
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Guest favourite
Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds, 4.5 bathrooms
19–24 Oct
4.96 out of 5 average rating, 111 reviews
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Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
14–19 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Guest house in Lanesborough
The Carriage House: Spotless, Charming 2 Bedroom
2 bedrooms, 2 beds, 1 bathroom
29 Oct – 3 Nov
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Home in Hancock
Grand 6BR Home by Jiminy | Hike • Hot Tub • Games
6 bedrooms, 14 beds, 5.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 65 reviews
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Superhost
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.79 out of 5 average rating, 103 reviews
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Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 78 reviews
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Top guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 330 reviews
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Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 46 reviews
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Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5 bedrooms, 4.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 39 reviews