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Search results; Over 1,000 homes in Lanesborough

Guest favourite

Home in Lanesborough

Mountain Blossom Retreat by Evergreen Home

3 bedrooms, 4 beds, 3.5 private bathrooms

21–26 Sept

$5,232 SGD for 5 nights

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4.98 out of 5 average rating, 42 reviews

Top guest favourite

Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

3 bedrooms, 4 beds

9–14 Sept

5.0 out of 5 average rating, 26 reviews

Top guest favourite

Home in Lanesborough

Berkshire Mountain House

4 bedrooms, 5 beds

14–19 Sept

$3,118 SGD for 5 nights

5.0 out of 5 average rating, 42 reviews

Home in Pittsfield

Cozy Lake Cottage

2 bedrooms, 2 beds

8–13 Sept

$1,582 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

3 bedrooms, 4 beds

31 Oct – 5 Nov

Free cancellation

4.85 out of 5 average rating, 300 reviews

Guest favourite

Home in Lanesborough

Elmwood Farmhouse

4 bedrooms, 7 beds

22–27 Sept

$2,134 SGD for 5 nights

4.9 out of 5 average rating, 124 reviews

Guest favourite

Cottage in Lanesborough

Lakefront Cottage | Private Dock, Kayaks & Firepit

2 bedrooms, 6 beds

14–19 Sept

Extended stay discount

4.77 out of 5 average rating, 13 reviews

Guest favourite

Home in Lanesborough

Berkshire Beauty + 6 BR/38 Acres mins from Jiminy

6 bedrooms, 10 beds

28 Sept – 3 Oct

4.96 out of 5 average rating, 111 reviews

Guest favourite

Home in Lanesborough

Historic Stone Church in The Berkshires

1 bedroom, 1 bed

13–18 Sept

$2,686 SGD for 5 nights

4.96 out of 5 average rating, 90 reviews

Top guest favourite

Home in Lanesborough

Berkshires Home-Near Williams College

3 bedrooms, 3 beds

10–15 Sept

$3,778 SGD for 5 nights

5.0 out of 5 average rating, 30 reviews

Top guest favourite

Home in Pittsfield

Marie’s Place unit 3

3 bedrooms, 3 beds

12–17 Sept

4.97 out of 5 average rating, 76 reviews

Top guest favourite

Home in Pittsfield

Berkshire Lakefront Home W/Pool-100%Renovated

6 bedrooms, 10 beds

26 Sept – 1 Oct

$6,708 SGD for 5 nights

4.98 out of 5 average rating, 84 reviews

Top guest favourite

Home in Hancock

Grand 6BR Home by Jiminy | Hike • Hot Tub • Games

6 bedrooms, 14 beds

27 Sept – 2 Oct

$2,730 SGD for 5 nights

4.97 out of 5 average rating, 64 reviews

Top guest favourite

Home in Lanesborough

Berkshire 6BR Estate • Pool, Hot Tub, Game Room

6 bedrooms, 9 beds

27 Sept – 2 Oct

$5,786 SGD for 5 nights

4.96 out of 5 average rating, 56 reviews

Guest favourite

Home in Lanesborough

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

4 bedrooms, 5 beds

9–14 Sept

4.97 out of 5 average rating, 78 reviews

Top guest favourite

Cabin in Lanesborough

Glamping- the Berkshires Hike on site! Car charger

3 bedrooms, 8 beds

7–12 Jan

Free cancellation

4.98 out of 5 average rating, 55 reviews

Guest favourite

Townhouse in Hancock

Beautiful Jiminy Peak Townhome Family Friendly

3 bedrooms, 5 beds

10–15 Sept

$1,182 SGD for 5 nights

4.83 out of 5 average rating, 109 reviews

Guest favourite

Cottage in Pittsfield

Lake Views & Dock Access - Pittsfield Cottage!

4 bedrooms, 6 beds

9–14 Sept

$3,915 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Guest favourite

Home in Pittsfield

Cantabile life in the Berkshires

3 bedrooms, 5 beds

11–16 Sept

$1,646 SGD for 5 nights

4.95 out of 5 average rating, 236 reviews