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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

$2,551 SGD for 5 nights

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4.85 out of 5 average rating, 296 reviews

Top guest favourite

Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

3 bedrooms, 4 beds, 2.5 bathrooms

8–13 Sept

$3,792 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

Home in Pittsfield

Cozy Berkshire Lakeside Retreat | Deck + Fire Pit

2 bedrooms, 2 beds, 1 bathroom

7–12 Jul

$2,569 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Pittsfield

A Ray of Sunshine-Lakefront-New Construction- ski

5 bedrooms, 4.5 bathrooms

26–31 Jul

$7,428 SGD for 5 nights

5.0 out of 5 average rating, 35 reviews

Top guest favourite

Home in Lanesborough

Historic Stone Church in The Berkshires

1 bedroom, 1 bed, 1.5 bathrooms

2–7 Aug

$2,741 SGD for 5 nights

4.98 out of 5 average rating, 81 reviews

Top guest favourite

Home in Lanesborough

Berkshire Mountain House

4 bedrooms, 5 beds, 3 bathrooms

11–16 Sept

$3,312 SGD for 5 nights

5.0 out of 5 average rating, 39 reviews

Home in Lanesborough

Casa Demeo, Private Berkshire Retreat

3 bedrooms, 3 beds, 3 bathrooms

27 Jul – 1 Aug

$2,208 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Guest favourite

Cottage in Lanesborough

The Grove Lakehouse

2 bedrooms, 6 beds, 1 bathroom

27 Jul – 1 Aug

$2,550 SGD for 5 nights

Free cancellation

4.86 out of 5 average rating, 7 reviews

Guest favourite

Home in Lanesborough

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

4 bedrooms, 5 beds, 1.5 bathrooms

16–21 Aug

$2,437 SGD for 5 nights

4.97 out of 5 average rating, 77 reviews

Guest favourite

Home in Lanesborough

Berkshires Home-Near Williams College

3 bedrooms, 3 beds, 2.5 bathrooms

25–30 Jul

$4,059 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

Guest favourite

Home in Lanesborough

Elmwood Farmhouse

4 bedrooms, 7 beds, 2.5 bathrooms

25–30 Aug

$2,266 SGD for 5 nights

4.9 out of 5 average rating, 119 reviews

Home in Lanesborough

New built - Split level house in the Berkshires

3 bedrooms, 5 beds, 3 bathrooms

8–13 Jul

$3,710 SGD for 5 nights

Top guest favourite

Home in Lanesborough

Lake, Berkshire Fave, Hot Tub, Lg Open LR, Family

4 bedrooms, 10 beds, 2 bathrooms

24–29 Aug

$3,277 SGD for 5 nights

4.99 out of 5 average rating, 71 reviews

Top guest favourite

Home in Lanesborough

Tranquil mid-century modern Berkshires retreat

3 bedrooms, 4 beds, 2.5 bathrooms

23–28 Aug

$3,162 SGD for 5 nights

4.99 out of 5 average rating, 132 reviews

Guest favourite

Home in Lanesborough

Berkshire Beauty + 6 BR/38 Acres mins from Jiminy

6 bedrooms, 10 beds, 4.5 bathrooms

1–6 Sept

$7,885 SGD for 5 nights

4.96 out of 5 average rating, 109 reviews

Top guest favourite

Home in Lanesborough

The Pond House

3 bedrooms, 4 beds, 1 bathroom

9–14 Dec

$1,876 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 49 reviews

Guest favourite

Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

2 bedrooms, 3 beds, 2 bathrooms

18–23 Jul

$5,285 SGD for 5 nights

4.92 out of 5 average rating, 104 reviews

Top guest favourite

Flat in Pittsfield

Marie's Place, Unit 1

3 bedrooms, 3 beds, 1 bathroom

12–17 Jul

$1,829 SGD for 5 nights

4.97 out of 5 average rating, 116 reviews

Flat in Cheshire

4 Bedrooms first floor home.

4 bedrooms, 6 beds, 1.5 bathrooms

7–12 Jul

$1,907 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews