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Search results; Over 1,000 homes in Sheffield

Guest favourite

Nature lodge in Sheffield

Sheffield Lodge - Greylock Room

1 bedroom, 1 bed, 1 private bathroom

12–17 Jul

$1,144 SGD for 5 nights

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4.92 out of 5 average rating, 77 reviews

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms, 3 beds

27 Jul – 1 Aug

$2,440 SGD for 5 nights

4.98 out of 5 average rating, 51 reviews

Guest favourite

Home in Sheffield

52-Acre Berkshires Farmhouse • Fire Pit + Trails

4 bedrooms, 9 beds

19–24 Jul

$3,079 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Guest favourite

Home in Sheffield

The Kellogg House in the Heart of The Berkshires

2 bedrooms, 2 queen beds

2–7 Aug

$2,135 SGD for 5 nights

4.98 out of 5 average rating, 65 reviews

Top guest favourite

Flat in Sheffield

Hideaway with Spectacular Berkshire Views

1 bedroom, 2 beds

24–29 Aug

$1,216 SGD for 5 nights

5.0 out of 5 average rating, 404 reviews

Top guest favourite

Home in Sheffield

All new mountain retreat near Great Barrington.

3 bedrooms, 5 beds

19–24 Jul

$4,648 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Home in Sheffield

Family friendly house with fenced yard & fire pit

3 bedrooms, 3 beds

26–31 Jul

4.96 out of 5 average rating, 25 reviews

Cabin in Sheffield

Log Cabin - playroom, fireplace, skiing - $0 fees

4 bedrooms, 8 beds

9–14 Aug

$2,807 SGD for 5 nights

4.78 out of 5 average rating, 343 reviews

Cottage in Sheffield

Charming Handcrafted Cottage in the Berkshires!

3 bedrooms, 5 beds

24–29 Aug

$1,836 SGD for 5 nights

4.79 out of 5 average rating, 100 reviews

Top guest favourite

Flat in Sheffield

Private Berkshire Barn Apartment

1 bedroom, 1 queen bed

27 Aug – 1 Sept

$949 SGD for 5 nights

4.94 out of 5 average rating, 178 reviews

Guest favourite

Home in Sheffield

Water-View Home in the Berkshires

3 bedrooms, 4 beds

23–28 Aug

$2,018 SGD for 5 nights

4.97 out of 5 average rating, 32 reviews

Guest favourite

Nature lodge in Sheffield

Sheffield Lodge - Ramblewood Master

1 bedroom, 1 king bed

12–17 Jul

$1,243 SGD for 5 nights

4.98 out of 5 average rating, 57 reviews

Top guest favourite

Guest suite in Sheffield

The Sunset Suite~Great South Berkshire Location!

1 queen bed

13–18 Jul

$1,457 SGD for 5 nights

5.0 out of 5 average rating, 91 reviews

Top guest favourite

Barn in New Marlborough

Hartsville Barn in the Berkshires

2 bedrooms, 2 king beds

14–19 Sept

$1,876 SGD for 5 nights

4.98 out of 5 average rating, 41 reviews

Guest favourite

Cottage in Sheffield

Cheerful 3-bedroom cottage with woodstove.

3 bedrooms, 4 beds

8–13 Sept

$1,733 SGD for 5 nights

4.93 out of 5 average rating, 189 reviews

Superhost

Guest house in Sheffield

The Cottage at 3 Sisters Farm

2 bedrooms, 2 queen beds

9–14 Jul

$1,895 SGD for 5 nights

4.83 out of 5 average rating, 12 reviews

Top guest favourite

Home in Sheffield

Belle Meade

2 bedrooms, 2 beds

21–26 Sept

$2,458 SGD for 5 nights

4.99 out of 5 average rating, 132 reviews

Guest favourite

Guest house in Sheffield

Dandelion Hill Farm Cottage

1 bedroom, 1 bed

9–14 Aug

$790 SGD for 5 nights

4.91 out of 5 average rating, 23 reviews

Top guest favourite

Home in Salisbury

Greystone at Twin Lakes

3 bedrooms, 3 beds

31 Jul – 5 Aug

$1,563 SGD for 5 nights

4.98 out of 5 average rating, 66 reviews