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Search results; Over 1,000 homes in Great Barrington

Top guest favourite

Home in Great Barrington

Walk to Town! Great Barrington 4-bedroom farmhouse

4 bedrooms, 4 beds, 2 private bathrooms

14–19 Sept

$2,981 SGD for 5 nights

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5.0 out of 5 average rating, 112 reviews

Guest favourite

Flat in Great Barrington

King Bed|ADA ROOM|2m Ski Resort

1 king bed

23–28 Aug

Extended stay discount

4.9 out of 5 average rating, 70 reviews

Top guest favourite

Home in Great Barrington

Stunning luxury home with pool

4 bedrooms, 4 beds

9–14 Sept

$3,895 SGD for 5 nights

4.99 out of 5 average rating, 93 reviews

Guest favourite

Flat in Great Barrington

King Bed|2mi Ski Resort|Fast Wi-Fi|Studio|

1 king bed

9–14 Aug

Extended stay discount

4.85 out of 5 average rating, 107 reviews

Guest favourite

Home in Great Barrington

Downtown Housatonic house –10 miles to Tangelwood

3 bedrooms, 4 beds

23–28 Aug

$1,951 SGD for 5 nights

4.89 out of 5 average rating, 9 reviews

Top guest favourite

Barn in New Marlborough

Hartsville Barn in the Berkshires

2 bedrooms, 2 king beds

27 Oct – 1 Nov

$1,831 SGD for 5 nights

4.98 out of 5 average rating, 43 reviews

Home in Great Barrington

Cozy Riverside Retreat in the Berkshires

3 bedrooms, 4 beds

23–28 Aug

$1,276 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

30 Aug – 4 Sept

$3,630 SGD for 5 nights

4.98 out of 5 average rating, 54 reviews

Guest favourite

Guest house in Great Barrington

Sweet Victorian in Housatonic

3 bedrooms, 4 beds

16–21 Aug

4.95 out of 5 average rating, 171 reviews

Superhost

Cabin in Monterey

Secluded cabin with babbling brook

3 bedrooms, 3 beds

9–14 Sept

$2,043 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

26–31 Oct

$833 SGD for 5 nights

4.95 out of 5 average rating, 421 reviews

Top guest favourite

Loft in Great Barrington

The Nest 5 min walk to downtown Great Barrington

1 bedroom, 1 queen bed

31 Aug – 5 Sept

$2,285 SGD for 5 nights

5.0 out of 5 average rating, 62 reviews

Guest favourite

Guest house in Great Barrington

Berkshires Guest Barn

2 bedrooms, 5 beds

16–21 Aug

$1,624 SGD for 5 nights

4.94 out of 5 average rating, 36 reviews

Top guest favourite

Room in Great Barrington

Cozy & Convenient

1 queen bed

10–15 Aug

$1,090 SGD for 5 nights

5.0 out of 5 average rating, 50 reviews

Guest favourite

Home in Great Barrington

Light & bright modern tree house

3 bedrooms, 3 beds

9–14 Aug

$3,587 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms, 3 beds

7–12 Sept

$1,928 SGD for 5 nights

4.98 out of 5 average rating, 54 reviews

Guest favourite

Cabin in Great Barrington

Kenyon's Cabin

2 bedrooms, 4 beds

9–14 Aug

$2,005 SGD for 5 nights

4.91 out of 5 average rating, 35 reviews

Rooms in Town of Hillsdale

Bellwether on Main, Passive House & AAC

2 bedrooms, 2 queen beds

9–14 Aug

$1,329 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Great Barrington

GB at your doorstep

3 bedrooms, 4 beds

31 Aug – 5 Sept

$3,065 SGD for 5 nights

4.94 out of 5 average rating, 138 reviews