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Search results; Over 1,000 homes in Lanesborough

Guest favourite

Home in Lanesborough

Historic Stone Church in The Berkshires

1 bedroom, 1 bed, 1.5 bathrooms

6–11 Sept

$2,698 SGD for 5 nights

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4.98 out of 5 average rating, 88 reviews

Top guest favourite

Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

3 bedrooms, 4 beds, 2.5 bathrooms

8–13 Sept

$3,665 SGD for 5 nights

5.0 out of 5 average rating, 26 reviews

Top guest favourite

Home in Lanesborough

Berkshire Mountain House

4 bedrooms, 5 beds, 3 bathrooms

14–19 Sept

$3,133 SGD for 5 nights

5.0 out of 5 average rating, 42 reviews

Guest favourite

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

3 bedrooms, 4 beds, 2.5 bathrooms

31 Oct – 5 Nov

Free cancellation

4.85 out of 5 average rating, 300 reviews

Guest favourite

Cottage in Lanesborough

Lakefront Cottage | Private Dock, Kayaks & Firepit

2 bedrooms, 6 beds, 1 bathroom

14–19 Sept

Extended stay discount

Free cancellation

4.77 out of 5 average rating, 13 reviews

Home in Pittsfield

Cozy Lake Cottage

2 bedrooms, 2 beds, 1.5 bathrooms

6–11 Sept

$1,590 SGD for 5 nights

New place to stay

Top guest favourite

Home in Lanesborough

The Pond House

3 bedrooms, 4 beds, 1 bathroom

20–25 Nov

$1,847 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 55 reviews

Guest favourite

Home in Lanesborough

Elmwood Farmhouse

4 bedrooms, 7 beds, 2.5 bathrooms

22–27 Sept

$2,203 SGD for 5 nights

4.9 out of 5 average rating, 124 reviews

Top guest favourite

Home in Lanesborough

Berkshires Home-Near Williams College

3 bedrooms, 3 beds, 2.5 bathrooms

7–12 Sept

5.0 out of 5 average rating, 30 reviews

Guest favourite

Home in Hancock

Family Lodge at Jiminy Peak - Pools & Adventure

4 bedrooms, 9 beds, 3 bathrooms

7–12 Sept

$2,688 SGD for 5 nights

4.95 out of 5 average rating, 58 reviews

Guest favourite

Home in Pittsfield

Cantabile life in the Berkshires

3 bedrooms, 5 beds, 2 bathrooms

11–16 Sept

$1,525 SGD for 5 nights

4.95 out of 5 average rating, 232 reviews

Guest favourite

Home in Lanesborough

Mountain Blossom Retreat by Evergreen Home

3 bedrooms, 4 beds, 3.5 bathrooms

21–26 Sept

$5,256 SGD for 5 nights

4.98 out of 5 average rating, 42 reviews

Top guest favourite

Flat in Pittsfield

Marie's Place

2 bedrooms, 2 queen beds, 1 bathroom

6–11 Sept

4.92 out of 5 average rating, 328 reviews

Top guest favourite

Flat in Pittsfield

Marie's Place, Unit 1

3 bedrooms, 3 beds, 1 bathroom

7–12 Sept

4.97 out of 5 average rating, 129 reviews

Guest favourite

Home in Lanesborough

Berkshire Beauty + 6 BR/38 Acres mins from Jiminy

6 bedrooms, 10 beds, 4.5 bathrooms

28 Sept – 3 Oct

4.96 out of 5 average rating, 111 reviews

Guest favourite

Home in Lanesborough

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

4 bedrooms, 5 beds, 1.5 bathrooms

4–9 Sept

$2,689 SGD for 5 nights

4.97 out of 5 average rating, 78 reviews

Superhost

Guest suite in Lanesborough

1bed rm. skier’s bliss 2 miles only 1 rd to slopes

1 bedroom, 2 beds, 1 bathroom

7–12 Sept

Free cancellation

4.79 out of 5 average rating, 100 reviews

Top guest favourite

Home in Pittsfield

Spacious 4 Br+ house in the heart of Berkshires

5 bedrooms, 5 beds, 2 bathrooms

9–14 Sept

$2,676 SGD for 5 nights

4.95 out of 5 average rating, 75 reviews

Top guest favourite

Home in Pittsfield

Solomon Ely Homestead set in walkable downtown

4 bedrooms, 4 beds, 1.5 bathrooms

8–13 Sept

$2,714 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 45 reviews