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Search results; Over 1,000 homes in Great Barrington

Top guest favourite

Cottage in Great Barrington

Artist Cottage

1 bedroom, 1 bed, 2 private bathrooms

7–12 Sept

$2,126 SGD for 5 nights

,

4.93 out of 5 average rating, 342 reviews

Top guest favourite

Cabin in Great Barrington

Modern Luxury Log Cabin

4 bedrooms, 6 beds, 3 bathrooms

19–24 Jul

$4,001 SGD for 5 nights

4.96 out of 5 average rating, 111 reviews

Guest favourite

Guest house in Great Barrington

Sweet Victorian in Housatonic

3 bedrooms, 4 beds, 1 bathroom

12–17 Jul

$2,400 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 165 reviews

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

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Chalet in Great Barrington

Berkshire "Zen" Cottage

3 bedrooms, 4 beds, 2 bathrooms

26–31 Jul

$2,210 SGD for 5 nights

4.96 out of 5 average rating, 81 reviews

Top guest favourite

Flat in Great Barrington

King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires

1 king bed, 1 bathroom

6–11 Jul

Extended stay discount

4.93 out of 5 average rating, 161 reviews

Superhost

Home in Monterey

Dog-Friendly Berkshires Retreat w/Fenced Yard

3 bedrooms, 3 beds, 2.5 bathrooms

28 Jul – 2 Aug

New home discount

New place to stay

Top guest favourite

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

3 bedrooms, 4 beds, 2 bathrooms

20–25 Sept

$2,696 SGD for 5 nights

4.99 out of 5 average rating, 308 reviews

Top guest favourite

Home in Great Barrington

Berkshires Black Abbey

3 bedrooms, 4 beds, 3 bathrooms

9–14 Aug

$3,800 SGD for 5 nights

5.0 out of 5 average rating, 36 reviews

Top guest favourite

Home in Great Barrington

Stunning luxury home with pool

4 bedrooms, 4 beds, 4.5 bathrooms

2–7 Aug

$7,772 SGD for 5 nights

4.99 out of 5 average rating, 92 reviews

Top guest favourite

Home in Great Barrington

Country Castle-Complete privacy-minutes from town

6 bedrooms, 8 beds, 3 bathrooms

4–9 Jul

$8,493 SGD for 5 nights

4.98 out of 5 average rating, 61 reviews

Guest favourite

Flat in Great Barrington

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

1 king bed, 1 bathroom

5–10 Jul

Extended stay discount

4.89 out of 5 average rating, 122 reviews

Guest favourite

Home in Great Barrington

Berkshire’s Best-hottub-fitness/gameroom

4 bedrooms, 4 beds, 2 bathrooms

23–28 Aug

$3,827 SGD for 5 nights

4.88 out of 5 average rating, 17 reviews

Guest favourite

Flat in Great Barrington

Kitchenette|King Bed|Couch

1 bedroom, 1 king bed, 1 bathroom

23–28 Aug

Extended stay discount

4.89 out of 5 average rating, 180 reviews

Superhost

Home in Great Barrington

The Docent's House - Honoring a Legacy

4 bedrooms, 5 beds, 2 bathrooms

26–31 Jul

$2,750 SGD for 5 nights

New place to stay

Guest favourite

Home in Great Barrington

Berkshires Retreat!

5 bedrooms, 9 beds, 2.5 bathrooms

9–14 Sept

$5,890 SGD for 5 nights

5.0 out of 5 average rating, 35 reviews

Top guest favourite

Home in Great Barrington

Private Home in The Berkshires (New Hot Tub!)

2 bedrooms, 2 queen beds, 1 bathroom

18–23 Jul

$2,090 SGD for 5 nights

4.99 out of 5 average rating, 124 reviews

Guest favourite

Room in Great Barrington

Comfy single for a night or two (Eco Airbnb)

1 single bed, 1.5 bathrooms

4–9 Jul

$593 SGD for 5 nights

4.91 out of 5 average rating, 47 reviews

Top guest favourite

Home in Great Barrington

Walk to Town! Great Barrington 4-bedroom farmhouse

4 bedrooms, 4 beds, 2 bathrooms

13–18 Oct

$3,086 SGD for 5 nights

5.0 out of 5 average rating, 110 reviews