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Search results; Over 1,000 homes in Stockbridge

Top guest favourite

Flat in Stockbridge

Historic,Famous,Iconic, Unforgettable Berks Escape

1 bedroom, 1 bed, 1 private bathroom

5–10 Sept

$2,057 SGD for 5 nights

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4.96 out of 5 average rating, 122 reviews

Top guest favourite

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

3 bedrooms, 4 beds, 2 bathrooms

20–25 Sept

$2,677 SGD for 5 nights

4.99 out of 5 average rating, 311 reviews

Guest favourite

Flat in Stockbridge

Stockbridge private apartment

1 bedroom, 2 beds, 1 bathroom

2–7 Aug

$1,652 SGD for 5 nights

4.92 out of 5 average rating, 92 reviews

Top guest favourite

Home in Stockbridge

Bright Stockbridge country home, near everything!

2 bedrooms, 2 queen beds, 2.5 bathrooms

13–18 Sept

$1,600 SGD for 5 nights

4.95 out of 5 average rating, 183 reviews

Guest favourite

Home in Great Barrington

Downtown Housatonic house –10 miles to Tangelwood

3 bedrooms, 4 beds, 2 bathrooms

23–28 Aug

$2,019 SGD for 5 nights

4.88 out of 5 average rating, 8 reviews

Top guest favourite

Guest house in Stockbridge

Cottage with exquisite views

4 bedrooms, 5 beds, 4 bathrooms

1–6 Sept

$4,749 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews

Top guest favourite

Home in Great Barrington

Berkshires Black Abbey

3 bedrooms, 4 beds, 3 bathrooms

9–14 Aug

$3,605 SGD for 5 nights

5.0 out of 5 average rating, 38 reviews

Guest favourite

Home in West Stockbridge

Exceptional Stockbridge Retreat

3 bedrooms, 4 beds, 1.5 bathrooms

25–30 Aug

$3,040 SGD for 5 nights

Free cancellation

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, 4.5 bathrooms

2–7 Aug

$7,569 SGD for 5 nights

4.99 out of 5 average rating, 92 reviews

Guest favourite

Cottage in Stockbridge

Quiet 2 BR cottage in the heart of the Berkshires

2 bedrooms, 3 beds, 1 bathroom

24–29 Aug

$2,373 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 44 reviews

Top guest favourite

Home in Lee

GreenHouse

2 bedrooms, 2 beds, 1.5 bathrooms

24–29 Oct

$1,419 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 132 reviews

Guest favourite

Home in Stockbridge

Your Stockbridge Getaway

5 bedrooms, 8 beds, 2.5 bathrooms

23–28 Aug

$5,434 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews

Home in Stockbridge

Light-filled Carpenter's Cottage

1 bedroom, 1 bed, 1 bathroom

26–31 Jul

$2,559 SGD for 5 nights

Free cancellation

New place to stay

Flat in Pittsfield

Mid-Berkshires

2 bedrooms, 2 beds, 1 bathroom

22–27 Aug

New place to stay

Top guest favourite

Room in Pittsfield

Cute Room with Bay Window in Downtown Victorian

2 beds, 3 bathrooms

26–31 Jul

Free cancellation

4.83 out of 5 average rating, 24 reviews

Guest favourite

Home in Stockbridge

Stockbridge Cape Near Tanglewood!

4 bedrooms, 5 beds, 2 bathrooms

23–28 Aug

$2,329 SGD for 5 nights

4.93 out of 5 average rating, 45 reviews

Guest favourite

Home in Lee

Spacious Central Berkshires Home for Groups

4 bedrooms, 5 beds, 2 bathrooms

13–18 Sept

$2,450 SGD for 5 nights

4.91 out of 5 average rating, 47 reviews

Guest favourite

Cabin in Stockbridge

Hip Stockbridge Cabin - A stroll to the lake

3 bedrooms, 5 beds, 1.5 bathrooms

30 Aug – 4 Sept

$4,083 SGD for 5 nights

4.89 out of 5 average rating, 246 reviews

Home in Stockbridge

New England Family Retreat in Stockbridge, MA

4 bedrooms, 5 beds, 3 bathrooms

26–31 Jul

$4,448 SGD for 5 nights

4.84 out of 5 average rating, 87 reviews