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Search results; Over 1,000 homes in Lanesborough

Descriptions are based on details hosts provide

Guest favourite

Cottage in Lanesborough

Stone School Cottage

2 bedrooms, 4 beds, 1 private bathroom

15–20 Jul

$1,516 SGD for 5 nights

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4.93 out of 5 average rating, 259 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

4.81 out of 5 average rating, 94 reviews

Top guest favourite

Guest house in Lanesborough

1820 carriage house near Mount Greylock

2 bedrooms, 2 beds, 1 bathroom

26–31 Oct

$973 SGD for 5 nights

5.0 out of 5 average rating, 20 reviews

Guest favourite

Cottage in Lanesborough

Lakeside cottage on a peninsula cove

3 bedrooms, 4 beds, 2.5 bathrooms

23–28 Aug

$2,549 SGD for 5 nights

4.85 out of 5 average rating, 296 reviews

Top guest favourite

Home in Pittsfield

Lake views from 3 decks with fire pit

4 bedrooms, 6 beds, 4 bathrooms

13–18 Sept

$4,565 SGD for 5 nights

4.94 out of 5 average rating, 47 reviews

Guest favourite

Home in Pittsfield

Lakehouse with a dock and kayaks

3 bedrooms, 3 beds, 1 bathroom

22–27 Sept

$1,888 SGD for 5 nights

4.92 out of 5 average rating, 48 reviews

Guest favourite

Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

2 bedrooms, 3 beds, 2 bathrooms

18–23 Jul

$5,122 SGD for 5 nights

4.92 out of 5 average rating, 105 reviews

Top guest favourite

Home in Lanesborough

Private dock and sunsets on the lake

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

Guest favourite

Home in Lanesborough

Berkshire Beauty + 6 BR/38 Acres mins from Jiminy

6 bedrooms, 10 beds, 4.5 bathrooms

1–6 Sept

$6,944 SGD for 5 nights

4.96 out of 5 average rating, 109 reviews

Top guest favourite

Home in Lanesborough

Cabin-in-the-woods feel on a pond

3 bedrooms, 4 beds, 1 bathroom

20–25 Nov

$1,875 SGD for 5 nights

4.96 out of 5 average rating, 51 reviews

Guest favourite

Home in Lanesborough

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

4 bedrooms, 5 beds, 1.5 bathrooms

16–21 Aug

$2,435 SGD for 5 nights

4.97 out of 5 average rating, 77 reviews

Guest favourite

Home in Pittsfield

The Guest House at Cottage Farm

3 bedrooms, 4 beds, 3 bathrooms

24–29 Aug

4.94 out of 5 average rating, 36 reviews

Guest favourite

Cottage in Pittsfield

Lake Views & Dock Access - Pittsfield Cottage!

4 bedrooms, 6 beds, 1.5 bathrooms

19–24 Jul

$3,993 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Cottage in Lanesborough

The Grove Lakehouse

2 bedrooms, 6 beds, 1 bathroom

24–29 Jul

4.86 out of 5 average rating, 7 reviews

Guest favourite

Home in Pittsfield

Cantabile life in the Berkshires

3 bedrooms, 5 beds, 2 bathrooms

26–31 Jul

$2,145 SGD for 5 nights

4.95 out of 5 average rating, 218 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 Pittsfield

1847 farmhouse with a wraparound porch

4 bedrooms, 4 beds, 1.5 bathrooms

24–29 Aug

$2,656 SGD for 5 nights

5.0 out of 5 average rating, 41 reviews

Top guest favourite

Flat in Pittsfield

Marie's Place, Unit 1

3 bedrooms, 3 beds, 1 bathroom

19–24 Jul

$1,731 SGD for 5 nights

4.97 out of 5 average rating, 118 reviews

Guest favourite

Home in Pittsfield

Lake views, a fire pit, and fireplace

2 bedrooms, 2 queen beds, 1 bathroom

5–10 Nov

$1,498 SGD for 5 nights

4.97 out of 5 average rating, 68 reviews