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Search results; Over 1,000 homes in Sheffield

Guest favourite

Nature lodge in Sheffield

Sheffield Lodge - Ramblewood Master

1 bedroom, 1 bed, 1 private bathroom

5–10 Jul

$1,337 SGD for 5 nights

,

4.98 out of 5 average rating, 57 reviews

Top guest favourite

Flat in Sheffield

Hideaway with Spectacular Berkshire Views

1 bedroom, 2 beds

24–29 Aug

$1,248 SGD for 5 nights

5.0 out of 5 average rating, 404 reviews

Guest favourite

Home in Sheffield

52-Acre Berkshires Farmhouse • Fire Pit + Trails

4 bedrooms, 9 beds

5–10 Jul

$2,928 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Flat in Sheffield

Private Berkshire Barn Apartment

1 bedroom, 1 queen bed

27 Aug – 1 Sept

$961 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 177 reviews

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms, 3 beds

6–11 Jul

$2,261 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 50 reviews

Top guest favourite

Flat in Canaan

West Main

2 bedrooms, 2 queen beds

20–25 Aug

$1,108 SGD for 5 nights

4.99 out of 5 average rating, 176 reviews

Top guest favourite

Room in Sheffield

Sheffield Lodge - Taconic Room

2 single beds

5–10 Jul

$1,070 SGD for 5 nights

4.98 out of 5 average rating, 54 reviews

Top guest favourite

Home in Sheffield

Family friendly house with fenced yard & fire pit

3 bedrooms, 3 beds

26–31 Jul

Free cancellation

4.96 out of 5 average rating, 24 reviews

Top guest favourite

Guest suite in Sheffield

The Sunset Suite~Great South Berkshire Location!

1 queen bed

6–11 Jul

$1,474 SGD for 5 nights

5.0 out of 5 average rating, 90 reviews

Superhost

Home in Sheffield

Berkshires Retreat w/ Pickleball – for Big Groups!

7 bedrooms, 8 beds

4–9 Jul

$6,568 SGD for 5 nights

New place to stay

Guest favourite

Guest house in Great Barrington

Berkshires Guest Barn

2 bedrooms, 5 beds

12–17 Jul

$1,681 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews

Top guest favourite

Home in Sheffield

Great Berkshire Getaway !

1 bedroom, 1 queen bed

4–9 Sept

$1,245 SGD for 5 nights

4.95 out of 5 average rating, 111 reviews

Guest favourite

Home in Sheffield

Charming Country House with a Hot Tub

4 bedrooms, 5 beds

13–18 Jul

$4,048 SGD for 5 nights

4.93 out of 5 average rating, 44 reviews

Top guest favourite

Barn in New Marlborough

Hartsville Barn in the Berkshires

2 bedrooms, 2 king beds

14–19 Sept

$1,879 SGD for 5 nights

4.98 out of 5 average rating, 40 reviews

Top guest favourite

Home in Sheffield

House Among Trees - A Perfect Holiday Getaway

3 bedrooms, 4 beds

9–14 Sept

$2,437 SGD for 5 nights

4.93 out of 5 average rating, 97 reviews

Top guest favourite

Home in Salisbury

Greystone at Twin Lakes

3 bedrooms, 3 beds

31 Jul – 5 Aug

$1,566 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 65 reviews

Guest favourite

Home in Sheffield

Cozy Cottage Route 7 Sheffield

1 bedroom

27 Jul – 1 Aug

$1,189 SGD for 5 nights

4.86 out of 5 average rating, 43 reviews

Guest favourite

Home in Sheffield

Perfect Peaceful Berkshire Location !

2 bedrooms, 2 queen beds

11–16 Sept

$1,375 SGD for 5 nights

4.91 out of 5 average rating, 128 reviews

Top guest favourite

Loft in Great Barrington

The Old Red Barn

1 bedroom, 1 queen bed

1–6 Sept

$1,448 SGD for 5 nights

4.99 out of 5 average rating, 361 reviews