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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

$1,601 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, 2.5 bathrooms

8–13 Sept

$3,797 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

Guest favourite

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

3 bedrooms, 4 beds, 2.5 bathrooms

23–28 Aug

$2,554 SGD for 5 nights

4.85 out of 5 average rating, 296 reviews

Guest favourite

Home in Pittsfield

A Ray of Sunshine-Lakefront-New Construction- ski

5 bedrooms, 4.5 bathrooms

26–31 Jul

$7,438 SGD for 5 nights

5.0 out of 5 average rating, 35 reviews

Home in Pittsfield

Cozy Berkshire Lakeside Retreat | Deck + Fire Pit

2 bedrooms, 2 beds, 1 bathroom

9–14 Jul

$2,316 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Lanesborough

Historic Stone Church in The Berkshires

1 bedroom, 1 bed, 1.5 bathrooms

2–7 Aug

$2,745 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

$3,356 SGD for 5 nights

5.0 out of 5 average rating, 39 reviews

Guest favourite

Home in Lanesborough

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

4 bedrooms, 10 beds, 2 bathrooms

24–29 Aug

$3,265 SGD for 5 nights

4.99 out of 5 average rating, 72 reviews

Guest favourite

Home in Lanesborough

Elmwood Farmhouse

4 bedrooms, 7 beds, 2.5 bathrooms

25–30 Aug

$2,274 SGD for 5 nights

4.9 out of 5 average rating, 119 reviews

Guest favourite

Home in Lanesborough

Berkshires Home-Near Williams College

3 bedrooms, 3 beds, 2.5 bathrooms

25–30 Jul

$4,064 SGD for 5 nights

5.0 out of 5 average rating, 25 reviews

Guest favourite

Cottage in Lanesborough

The Grove Lakehouse

2 bedrooms, 6 beds, 1 bathroom

27 Jul – 1 Aug

$2,553 SGD for 5 nights

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

$2,440 SGD for 5 nights

4.97 out of 5 average rating, 77 reviews

Home in Lanesborough

Casa Demeo, Private Berkshire Retreat

3 bedrooms, 3 beds, 3 bathrooms

1–6 Sept

$2,402 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Lanesborough

Tranquil mid-century modern Berkshires retreat

3 bedrooms, 4 beds, 2.5 bathrooms

23–28 Aug

$3,091 SGD for 5 nights

4.99 out of 5 average rating, 132 reviews

Guest favourite

Home in Pittsfield

Beautiful Lake-view Getaway!

2 bedrooms, 2 queen beds, 1 bathroom

5–10 Nov

$1,425 SGD for 5 nights

4.97 out of 5 average rating, 67 reviews

Guest favourite

Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

2 bedrooms, 3 beds, 2 bathrooms

18–23 Jul

$5,151 SGD for 5 nights

4.92 out of 5 average rating, 104 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

19–24 Jul

$809 SGD for 5 nights

4.81 out of 5 average rating, 93 reviews

Top guest favourite

Home in Pittsfield

Solomon Ely Homestead set in walkable downtown

4 bedrooms, 4 beds, 1.5 bathrooms

9–14 Jul

$2,676 SGD for 5 nights

5.0 out of 5 average rating, 41 reviews

Top guest favourite

Home in Lanesborough

The Pond House

3 bedrooms, 4 beds, 1 bathroom

9–14 Dec

$1,879 SGD for 5 nights

4.96 out of 5 average rating, 50 reviews