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Search results; Over 1,000 homes in Sheffield

Top guest favourite

Flat in Sheffield

Hideaway with Spectacular Berkshire Views

1 bedroom, 2 beds, 1 private bathroom

4–9 Aug

$1,241 SGD for 5 nights

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5.0 out of 5 average rating, 399 reviews

Guest favourite

Home in Sheffield

Water-View Home in the Berkshires

3 bedrooms4 beds, 2 bathrooms,

23–28 Jun

$2,102 SGD for 5 nights

5.0 out of 5 average rating, 30 reviews

Top guest favourite

Home in Sheffield

Belle Meade

2 bedrooms2 beds, 2 bathrooms,

8–13 Jun

$2,426 SGD for 5 nights

4.99 out of 5 average rating, 128 reviews

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms3 beds, 2 bathrooms,

8–13 Jun

$2,409 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 49 reviews

Guest favourite

Home in Sheffield

All new mountain retreat near Great Barrington.

3 bedrooms5 beds, 2 bathrooms,

2–7 Jun

$3,540 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in Sheffield

Cozy Cottage Route 7 Sheffield

1 bedroom1 bathroom,

8–13 Jun

$941 SGD for 5 nights

4.85 out of 5 average rating, 41 reviews

Top guest favourite

Home in Sheffield

Family friendly house with fenced yard & fire pit

3 bedrooms3 beds, 2 bathrooms,

14–19 Jun

$2,769 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 21 reviews

Guest favourite

Home in Sheffield

The Kellogg House in the Heart of The Berkshires

2 bedrooms2 queen beds, 1 bathroom,

21–26 Jun

$2,108 SGD for 5 nights

4.98 out of 5 average rating, 64 reviews

Cabin in Sheffield

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

4 bedrooms8 beds, 3 bathrooms,

1–6 Jun

4.78 out of 5 average rating, 339 reviews

Top guest favourite

Flat in Sheffield

Private Berkshire Barn Apartment

1 bedroom1 queen bed, 1 bathroom,

4–9 Aug

$961 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 173 reviews

Superhost

Home in Sheffield

52-Acre Berkshires Farmhouse • Fire Pit + Trails

4 bedrooms9 beds, 2.5 bathrooms,

7–12 Jun

5.0 out of 5 average rating, 4 reviews

Guest favourite

Cottage in Sheffield

Cheerful 3-bedroom cottage with woodstove.

3 bedrooms4 beds, 2.5 bathrooms,

8–13 Sept

$1,734 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 181 reviews

Top guest favourite

Guest suite in Sheffield

The Sunset Suite~Great South Berkshire Location!

1 queen bed1 bathroom,

3–8 Jun

$1,363 SGD for 5 nights

5.0 out of 5 average rating, 89 reviews

Top guest favourite

Guest house in Sheffield

Spring Fling at the Black Bear Bungalow

1 bedroom1 queen bed, 1 bathroom,

25–30 May

$1,348 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 28 reviews

Guest favourite

Home in Sheffield

Berkshire Getaway~ No Pet Fee! Walk to Distillery

3 bedrooms3 beds, 2 bathrooms,

7–12 Jun

$2,401 SGD for 5 nights

4.89 out of 5 average rating, 92 reviews

Top guest favourite

Home in Sheffield

Beautiful Berkshires Home | Perfect For 3 Families

4 bedrooms9 beds, 2 bathrooms,

7–12 Jun

$3,763 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 26 reviews

Top guest favourite

Cottage in Sheffield

The Blue Elm A Historic Country Cottage

1 bedroom2 beds, 1.5 bathrooms,

21–26 Jun

$1,543 SGD for 5 nights

5.0 out of 5 average rating, 87 reviews

Guest favourite

Home in Sheffield

Great Berkshire Getaway !

1 bedroom1 queen bed, 1 bathroom,

4–9 Sept

$1,227 SGD for 5 nights

4.95 out of 5 average rating, 110 reviews

Top guest favourite

Home in New Marlborough

Scenic Berkshire retreat near Great Barrington

2 bedrooms2 beds, 1 bathroom,

1–6 Jun

$2,482 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews