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Search results; Over 1,000 homes in Lanesborough

Guest favourite

Cottage in Lanesborough

Stone School Cottage

2 bedrooms, 4 beds, 1 private bathroom

12–17 Jul

$1,599 SGD for 5 nights

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4.93 out of 5 average rating, 258 reviews

Top guest favourite

Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

3 bedrooms, 4 beds

8–13 Sept

$3,792 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 23 reviews

Guest favourite

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

3 bedrooms, 4 beds

9–14 Aug

$2,551 SGD for 5 nights

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Free cancellation

4.85 out of 5 average rating, 296 reviews

Home in Pittsfield

Cozy Berkshire Lakeside Retreat | Deck + Fire Pit

2 bedrooms, 2 beds

7–12 Jul

$2,569 SGD for 5 nights

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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

26–31 Jul

$7,428 SGD for 5 nights

5.0 out of 5 average rating, 35 reviews

Top guest favourite

Home in Lanesborough

Berkshire Mountain House

4 bedrooms, 5 beds

11–16 Sept

$3,312 SGD for 5 nights

5.0 out of 5 average rating, 39 reviews

Guest favourite

Cottage in Lanesborough

The Grove Lakehouse

2 bedrooms, 6 beds

27 Jul – 1 Aug

$2,549 SGD for 5 nights

Pay $0 today

Free cancellation

4.86 out of 5 average rating, 7 reviews

Guest favourite

Home in Lanesborough

Berkshires Home-Near Williams College

3 bedrooms, 3 beds

25–30 Jul

$4,058 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

Top guest favourite

Home in Lanesborough

Historic Stone Church in The Berkshires

1 bedroom, 1 bed

2–7 Aug

$2,741 SGD for 5 nights

4.98 out of 5 average rating, 81 reviews

Guest favourite

Home in Lanesborough

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

4 bedrooms, 5 beds

16–21 Aug

$2,437 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 77 reviews

Home in Lanesborough

Casa Demeo, Private Berkshire Retreat

3 bedrooms, 3 beds

27 Jul – 1 Aug

$2,208 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Lanesborough

Elmwood Farmhouse

4 bedrooms, 7 beds

12–17 Aug

$2,373 SGD for 5 nights

4.9 out of 5 average rating, 119 reviews

Top guest favourite

Home in Lanesborough

Tranquil mid-century modern Berkshires retreat

3 bedrooms, 4 beds

23–28 Aug

$3,161 SGD for 5 nights

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Free cancellation

4.99 out of 5 average rating, 132 reviews

Top guest favourite

Home in Lanesborough

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

4 bedrooms, 10 beds

24–29 Aug

$3,276 SGD for 5 nights

4.99 out of 5 average rating, 71 reviews

Guest favourite

Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

2 bedrooms, 3 beds

7–12 Jul

$5,284 SGD for 5 nights

4.92 out of 5 average rating, 104 reviews

Guest favourite

Home in Lanesborough

Berkshire Beauty + 6 BR/38 Acres mins from Jiminy

6 bedrooms, 10 beds

1–6 Sept

$7,885 SGD for 5 nights

4.96 out of 5 average rating, 109 reviews

Top guest favourite

Home in Pittsfield

Lakefront home in the heart of the Berkshires

4 bedrooms, 6 beds

13–18 Sept

$4,568 SGD for 5 nights

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Free cancellation

4.93 out of 5 average rating, 46 reviews

Home in Lanesborough

New built - Split level house in the Berkshires

3 bedrooms, 5 beds

9–14 Jul

$3,710 SGD for 5 nights

Pay $0 today

Free cancellation

Top guest favourite

Home in Hancock

Family Lodge at Jiminy Peak - Pools & Adventure

4 bedrooms, 9 beds

11–16 Jul

$4,705 SGD for 5 nights

4.96 out of 5 average rating, 50 reviews