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Search results; Over 1,000 homes in Great Barrington

Guest favourite

Cottage in Great Barrington

The Cottage at The Barrington House

1 bedroom, 1 bed, 1 private bathroom

22–27 Aug

$1,728 SGD for 5 nights

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4.94 out of 5 average rating, 214 reviews

Top guest favourite

Cottage in Great Barrington

Artist Cottage

1 bedroom, 1 queen bed, 2 bathrooms

13–18 Sept

$2,074 SGD for 5 nights

4.93 out of 5 average rating, 349 reviews

Top guest favourite

Flat in Great Barrington

King Bed |Wi-Fi| 2m to Ski Resort

1 king bed, 1 bathroom

30 Aug – 4 Sept

$738 SGD for 5 nights

Extended stay discount

4.92 out of 5 average rating, 212 reviews

Top guest favourite

Home in Great Barrington

Stunning luxury home with pool

4 bedrooms, 4 beds, 4.5 bathrooms

9–14 Sept

4.99 out of 5 average rating, 93 reviews

Guest favourite

Home in Great Barrington

Downtown Housatonic house –10 miles to Tangelwood

3 bedrooms, 4 beds, 2 bathrooms

23–28 Aug

$1,945 SGD for 5 nights

4.89 out of 5 average rating, 9 reviews

Guest favourite

Guest house in Great Barrington

Sweet Victorian in Housatonic

3 bedrooms, 4 beds, 1 bathroom

16–21 Aug

4.95 out of 5 average rating, 171 reviews

Home in Great Barrington

Cozy Riverside Retreat in the Berkshires

3 bedrooms, 4 beds, 1 bathroom

23–28 Aug

$1,272 SGD for 5 nights

4.48 out of 5 average rating, 27 reviews

Guest favourite

Cottage in Egremont

Kayak on Prospect Lake, Paddle Boards, Swim Dock+!

3 bedrooms, 5 beds, 1 bathroom

12–17 Sept

$3,235 SGD for 5 nights

4.98 out of 5 average rating, 54 reviews

Guest favourite

Home in Great Barrington

Berkshire’s Best-hottub-fitness/gameroom

4 bedrooms, 4 beds, 2 bathrooms

23–28 Aug

$3,598 SGD for 5 nights

4.91 out of 5 average rating, 22 reviews

Top guest favourite

Loft in Great Barrington

The Nest 5 min walk to downtown Great Barrington

1 bedroom, 1 queen bed, 1 bathroom

31 Aug – 5 Sept

$2,278 SGD for 5 nights

5.0 out of 5 average rating, 63 reviews

Superhost

Cabin in Monterey

Secluded cabin with babbling brook

3 bedrooms, 3 beds, 1 bathroom

9–14 Sept

$2,037 SGD for 5 nights

4.87 out of 5 average rating, 256 reviews

Top guest favourite

Flat in Great Barrington

Private En Suite in Beautiful Victorian

1 bedroom, 1 queen bed, 1 bathroom

26–31 Oct

$830 SGD for 5 nights

4.95 out of 5 average rating, 421 reviews

Guest favourite

Guest house in Great Barrington

Berkshires Guest Barn

2 bedrooms, 5 beds, 1 bathroom

16–21 Aug

$1,619 SGD for 5 nights

4.94 out of 5 average rating, 36 reviews

Guest favourite

Cabin in Great Barrington

Kenyon's Cabin

2 bedrooms, 4 beds, 1 bathroom

9–14 Aug

$1,999 SGD for 5 nights

4.91 out of 5 average rating, 35 reviews

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms, 3 beds, 2 bathrooms

7–12 Sept

$1,922 SGD for 5 nights

4.98 out of 5 average rating, 54 reviews

Top guest favourite

Home in Great Barrington

GB at your doorstep

3 bedrooms, 4 beds, 2 bathrooms

31 Aug – 5 Sept

$3,056 SGD for 5 nights

4.94 out of 5 average rating, 138 reviews

Rooms in Town of Hillsdale

Bellwether on Main, Passive House & AAC

2 bedrooms, 2 queen beds, 2 bathrooms

9–14 Aug

$1,325 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Cottage in Monterey

Beaver Lodge

3 bedrooms, 3 queen beds, 1.5 bathrooms

10–15 Sept

$1,739 SGD for 5 nights

5.0 out of 5 average rating, 83 reviews

Guest favourite

Home in Great Barrington

Light & bright modern tree house

3 bedrooms, 3 beds, 3.5 bathrooms

10–15 Aug

$3,576 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews