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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

23–28 Aug

$2,549 SGD for 5 nights

,

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

$3,789 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

Top guest favourite

Home in Pittsfield

Berkshire Lakefront Home W/Pool-100%Renovated

6 bedrooms, 10 beds, 4.5 bathrooms

26 Sept – 1 Oct

$6,842 SGD for 5 nights

4.98 out of 5 average rating, 81 reviews

Guest favourite

Home in Pittsfield

A Ray of Sunshine-Lakefront-New Construction- ski

5 bedrooms, 4.5 bathrooms

26–31 Jul

$7,423 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

$2,739 SGD for 5 nights

4.98 out of 5 average rating, 82 reviews

Top guest favourite

Home in Lanesborough

Berkshire Mountain House

4 bedrooms, 5 beds, 3 bathrooms

11–16 Sept

$3,309 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, 1 bathroom

24–29 Jul

Extended stay discount

Free cancellation

4.86 out of 5 average rating, 7 reviews

Guest favourite

Home in Lanesborough

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

4 bedrooms, 10 beds, 2 bathrooms

24–29 Aug

$3,235 SGD for 5 nights

4.99 out of 5 average rating, 72 reviews

Guest favourite

Home in Lanesborough

Berkshires Home-Near Williams College

3 bedrooms, 3 beds, 2.5 bathrooms

24–29 Jul

$3,472 SGD for 5 nights

5.0 out of 5 average rating, 26 reviews

Guest favourite

Home in Lanesborough

Elmwood Farmhouse

4 bedrooms, 7 beds, 2.5 bathrooms

25–30 Aug

$2,259 SGD for 5 nights

4.9 out of 5 average rating, 119 reviews

Guest favourite

Townhouse in Hancock

Jiminy Peak Slopeside Getaway • Ski & Adventure

2 bedrooms, 3 beds, 2 bathrooms

19–24 Jul

5.0 out of 5 average rating, 12 reviews

Home in Lanesborough

New built - Split level house in the Berkshires

3 bedrooms, 5 beds, 3 bathrooms

21–26 Jul

$3,707 SGD for 5 nights

Guest favourite

Home in Lanesborough

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

4 bedrooms, 5 beds, 1.5 bathrooms

16–21 Aug

$2,435 SGD for 5 nights

4.97 out of 5 average rating, 77 reviews

Top guest favourite

Home in Lanesborough

Tranquil mid-century modern Berkshires retreat

3 bedrooms, 4 beds, 2.5 bathrooms

23–28 Aug

$3,075 SGD for 5 nights

4.99 out of 5 average rating, 132 reviews

Guest favourite

Cottage in Lanesborough

Stone School Cottage

2 bedrooms, 4 beds, 1 bathroom

15–20 Jul

$1,516 SGD for 5 nights

4.93 out of 5 average rating, 259 reviews

Top guest favourite

Home in Lanesborough

The Pond House

3 bedrooms, 4 beds, 1 bathroom

20–25 Nov

$1,875 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 51 reviews

Guest favourite

Home in Hancock

Comfortable Berkshires retreat on mtn resort, SISO

4 bedrooms, 12 beds, 3 bathrooms

2–7 Aug

4.92 out of 5 average rating, 48 reviews

Guest favourite

Guest suite in Lanesborough

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

1 bedroom, 2 beds, 1 bathroom

26–31 Jul

$792 SGD for 5 nights

Free cancellation

4.81 out of 5 average rating, 94 reviews

Top guest favourite

Home in Hancock

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

6 bedrooms, 14 beds, 5.5 bathrooms

19–24 Jul

$3,254 SGD for 5 nights

4.96 out of 5 average rating, 55 reviews