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Search results; Over 1,000 homes in Lanesborough

Guest favourite

Home in Lanesborough

Elmwood Farmhouse

4 bedrooms, 7 beds, 2.5 private bathrooms

25–30 Aug

$2,278 SGD for 5 nights

,

4.9 out of 5 average rating, 117 reviews

Top guest favourite

Home in Lanesborough

The Pond House

3 bedrooms4 beds, 1 bathroom,

14–19 Nov

$1,787 SGD for 5 nights

4.96 out of 5 average rating, 49 reviews

Guest favourite

Home in Pittsfield

Beautiful Lake-view Getaway!

2 bedrooms2 queen beds, 1 bathroom,

14–19 Jun

$1,309 SGD for 5 nights

4.97 out of 5 average rating, 63 reviews

Top guest favourite

Home in Lanesborough

Historic Stone Church in The Berkshires

1 bedroom1 bed, 1.5 bathrooms,

18–23 Jun

$2,723 SGD for 5 nights

4.97 out of 5 average rating, 79 reviews

Top guest favourite

Room in Pittsfield

Large guest suite w/private bath in the Berkshires

2 beds1 bathroom,

7–12 Jun

$704 SGD for 5 nights

4.98 out of 5 average rating, 450 reviews

Guest favourite

Cottage in Lanesborough

The Grove Lakehouse

2 bedrooms6 beds, 1 bathroom,

13–18 Aug

$2,576 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Home in Lanesborough

Berkshire Mountain House

4 bedrooms5 beds, 3 bathrooms,

20–25 Jul

$3,875 SGD for 5 nights

5.0 out of 5 average rating, 36 reviews

Top guest favourite

Home in Lanesborough

Tranquil mid-century modern Berkshires retreat

3 bedrooms4 beds, 2.5 bathrooms,

23–28 Aug

$3,139 SGD for 5 nights

4.99 out of 5 average rating, 132 reviews

Guest favourite

Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

2 bedrooms3 beds, 2 bathrooms,

7–12 Jun

$3,453 SGD for 5 nights

4.93 out of 5 average rating, 100 reviews

Top guest favourite

Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

3 bedrooms4 beds, 2.5 bathrooms,

5–10 Jun

$3,058 SGD for 5 nights

5.0 out of 5 average rating, 22 reviews

Top guest favourite

Guest suite in Pittsfield

Newly Renovated Red Door Annex

1 bedroom1 queen bed, 1 bathroom,

14–19 Jun

$817 SGD for 5 nights

4.91 out of 5 average rating, 113 reviews

Guest favourite

Cottage in Lanesborough

Stone School Cottage

2 bedrooms4 beds, 1 bathroom,

4–9 Jun

$1,452 SGD for 5 nights

4.93 out of 5 average rating, 255 reviews

Top guest favourite

Guest house in Lanesborough

The Carriage House: Spotless, Charming 2 Bedroom

2 bedrooms2 beds, 1 bathroom,

26–31 Oct

$1,046 SGD for 5 nights

5.0 out of 5 average rating, 20 reviews

Guest favourite

Flat in Pittsfield

HawksNest: quiet 2BR apt, heart of the Berkshires

2 bedrooms2 beds, 1.5 bathrooms,

1–6 Nov

$599 SGD for 5 nights

4.84 out of 5 average rating, 194 reviews

Top guest favourite

Farm stay in Pittsfield

Private 2nd-floor studio on a working produce farm

1 bedroom1 bed, 1 bathroom,

14–19 Jun

4.99 out of 5 average rating, 303 reviews

Top guest favourite

Cottage in Lanesborough

Pontoosuc Lakeshore

2 bedrooms3 beds, 1.5 bathrooms,

7–12 Jun

$2,987 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

Guest favourite

Cottage in Pittsfield

Charming lakeview cottage w/ kayaks, Richmond Pond

3 bedrooms4 beds, 1 bathroom,

9–14 Jun

$1,614 SGD for 5 nights

4.8 out of 5 average rating, 49 reviews

Guest favourite

Home in Lanesborough

Cozy Berkshire lake house

4 bedrooms4 beds, 2 bathrooms,

11–16 Jun

$3,659 SGD for 5 nights

4.91 out of 5 average rating, 44 reviews

Top guest favourite

Cottage in Lanesborough

Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak

2 bedrooms2 beds, 2 bathrooms,

31 Dec – 5 Jan

$2,522 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews