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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite

Flat in Great Barrington

King Bed|Wi-Fi|2m Ski Resort

Studio, 1 bed, 1 private bathroom

24–29 Oct

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4.87 out of 5 average rating, 255 reviews

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Home in Great Barrington

Riverside Retreat in the Berkshires

3 bedrooms, 4 beds

25–30 Oct

$1,408 SGD for 5 nights

Free cancellation

4.62 out of 5 average rating, 39 reviews

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Guest favourite

Guest house in Great Barrington

Sweet Victorian in Housatonic

3 bedrooms, 4 beds

18–23 Oct

$1,466 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 177 reviews

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Guest favourite

Flat in Great Barrington

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

1 king bed

4–9 Oct

Extended stay discount

4.92 out of 5 average rating, 224 reviews

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Top guest favourite

Home in Great Barrington

Seekonk Hill

2 bedrooms, 2 queen beds

26–31 Oct

$2,096 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 48 reviews

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Top guest favourite

Home in Great Barrington

Prime location for the best of the Berkshires

2 bedrooms, 2 queen beds

10–15 Nov

$1,696 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 141 reviews

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Top guest favourite

Home in Great Barrington

Modern Victorian- Walk to Town

4 bedrooms, 7 beds

18–23 Oct

$2,084 SGD for 5 nights

4.97 out of 5 average rating, 142 reviews

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Home in Great Barrington

Mountain Views + Scenic Berkshires Hideaway

3 bedrooms, 6 beds

1–6 Oct

$2,741 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

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Guest favourite

Home in Great Barrington

Charming, view, large deck, private/walk downtown

3 bedrooms, 4 beds

17–22 Oct

$2,852 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 102 reviews

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Top guest favourite

Barn in New Marlborough

Hartsville Barn in the Berkshires

2 bedrooms, 2 king beds

20–25 Oct

$1,799 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 52 reviews

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Top guest favourite

Home in Great Barrington

Sauna + Hot Tub Escape | Private & Pet Friendly

3 bedrooms, 4 beds

30 Oct – 4 Nov

$3,534 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 56 reviews

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Top guest favourite

Home in Great Barrington

RENOVATED BERKSHIRE COUNTRY CASTLE

3 bedrooms, 3 beds

12–17 Oct

$2,391 SGD for 5 nights

4.97 out of 5 average rating, 58 reviews

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Superhost

Home in Great Barrington

Relaxing Housatonic Retreat

3 bedrooms, 3 beds

25–30 Oct

$1,118 SGD for 5 nights

Free cancellation

4.7 out of 5 average rating, 128 reviews

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Superhost

Home in Great Barrington

Prime Location, Recently Redesigned, Riverfront!

4 bedrooms, 6 beds

1–6 Oct

4.9 out of 5 average rating, 10 reviews

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Hotel room in Lee

Endless Family Fun: Pools, Arcade Room & Mini Golf

2 bedrooms

4–9 Oct

$712 SGD for 5 nights

Free cancellation

4.67 out of 5 average rating, 36 reviews

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Guest favourite

Home in Great Barrington

GB at your doorstep

3 bedrooms, 4 beds

26–31 Oct

$2,039 SGD for 5 nights

4.94 out of 5 average rating, 141 reviews

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Guest favourite

Home in Great Barrington

River Cottage - Riverfront Home in Walkable Commun

3 bedrooms, 3 beds

1–6 Oct

$3,594 SGD for 5 nights

4.96 out of 5 average rating, 70 reviews

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Guest favourite

Home in Great Barrington

Berkshires Family Oasis with Hot Tub, Patio, Gym

4 bedrooms, 7 beds

11–16 Oct

$4,101 SGD for 5 nights

4.98 out of 5 average rating, 51 reviews

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Guest favourite

Cottage in Sheffield

Cheerful 3-bedroom cottage with woodstove.

3 bedrooms, 3 beds

24–29 Oct

$1,435 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 196 reviews