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Search results; Over 1,000 homes in Stockbridge

Guest favourite

Home in Stockbridge

Rabbit Run in the heart of Stockbridge Village

3 bedrooms, 4 beds, 2 private bathrooms

19–24 Jul

$2,246 SGD for 5 nights

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4.89 out of 5 average rating, 123 reviews

Top guest favourite

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

3 bedrooms, 4 beds

20–25 Sept

$2,682 SGD for 5 nights

4.99 out of 5 average rating, 311 reviews

Top guest favourite

Home in Stockbridge

Bright Stockbridge country home, near everything!

2 bedrooms, 2 queen beds

13–18 Sept

$1,599 SGD for 5 nights

4.95 out of 5 average rating, 183 reviews

Guest favourite

Flat in Stockbridge

Stockbridge private apartment

1 bedroom, 2 beds

2–7 Aug

$1,675 SGD for 5 nights

4.92 out of 5 average rating, 92 reviews

Top guest favourite

Cottage in Stockbridge

Quiet 2 BR cottage in the heart of the Berkshires

2 bedrooms, 3 beds

24–29 Aug

$2,372 SGD for 5 nights

4.95 out of 5 average rating, 43 reviews

Guest favourite

Home in Stockbridge

Stockbridge Cape Near Tanglewood!

4 bedrooms, 5 beds

23–28 Aug

$2,322 SGD for 5 nights

4.93 out of 5 average rating, 45 reviews

Top guest favourite

Home in Lee

GreenHouse

2 bedrooms, 2 beds

24–29 Oct

$1,420 SGD for 5 nights

4.99 out of 5 average rating, 132 reviews

Top guest favourite

Home in Pittsfield

Cozy cottage on peaceful pond

2 bedrooms, 2 beds

27 Aug – 1 Sept

5.0 out of 5 average rating, 27 reviews

Flat in Pittsfield

Mid-Berkshires

2 bedrooms, 2 beds

22–27 Aug

New home discount

New place to stay

Top guest favourite

Guest house in Stockbridge

Cottage with exquisite views

4 bedrooms, 5 beds

1–6 Sept

$4,747 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews

Guest favourite

Home in Great Barrington

Downtown Housatonic house –10 miles to Tangelwood

3 bedrooms, 4 beds

23–28 Aug

$2,018 SGD for 5 nights

4.83 out of 5 average rating, 6 reviews

Guest favourite

Home in West Stockbridge

Exceptional Stockbridge Retreat

3 bedrooms, 4 beds

25–30 Aug

$3,038 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews

Top guest favourite

Home in Great Barrington

Stunning luxury home with pool

4 bedrooms, 4 beds

2–7 Aug

$7,565 SGD for 5 nights

4.99 out of 5 average rating, 92 reviews

Top guest favourite

Home in Great Barrington

Berkshires Black Abbey

3 bedrooms, 4 beds

9–14 Aug

$3,669 SGD for 5 nights

5.0 out of 5 average rating, 36 reviews

Top guest favourite

Cabin in Stockbridge

Lakeshore cabin with beach and dock

3 bedrooms, 5 beds

3–8 Sept

$4,400 SGD for 5 nights

4.98 out of 5 average rating, 63 reviews

Top guest favourite

Guest house in Stockbridge

Modern studio with views of the treetops

2 beds

7–12 Sept

$1,342 SGD for 5 nights

4.96 out of 5 average rating, 301 reviews

Guest favourite

Home in Lee

Spacious Central Berkshires Home for Groups

4 bedrooms, 5 beds

7–12 Sept

$2,449 SGD for 5 nights

4.91 out of 5 average rating, 46 reviews

Top guest favourite

Guest house in Stockbridge

Bitty Berkshire Bungalow

1 bedroom, 1 queen bed

18–23 Sept

$963 SGD for 5 nights

4.98 out of 5 average rating, 46 reviews

Top guest favourite

Home in Lee

Berkshire 4 season home

3 bedrooms, 3 queen beds

25–30 Oct

$1,710 SGD for 5 nights

4.98 out of 5 average rating, 248 reviews