We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Sheffield

Nature lodge in Sheffield

Sheffield Lodge

6 bedrooms, 7 beds, 5 private bathrooms

24–29 Aug

$7,731 SGD for 5 nights

,

5.0 out of 5 average rating, 14 reviews

Top guest favourite

Flat in Sheffield

Hideaway with Spectacular Berkshire Views

1 bedroom, 2 beds

24–29 Aug

$1,213 SGD for 5 nights

5.0 out of 5 average rating, 408 reviews

Guest favourite

Home in Sheffield

52-Acre Berkshires Farmhouse • Fire Pit + Trails

4 bedrooms, 9 beds

16–21 Aug

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in Sheffield

The Kellogg House in the Heart of The Berkshires

2 bedrooms, 2 queen beds

27 Aug – 1 Sept

$2,146 SGD for 5 nights

4.99 out of 5 average rating, 67 reviews

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms, 3 beds

7–12 Sept

$1,936 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 54 reviews

Cabin in Sheffield

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

4 bedrooms, 8 beds

9–14 Aug

4.77 out of 5 average rating, 347 reviews

Cottage in Sheffield

Charming Handcrafted Cottage in the Berkshires!

3 bedrooms, 5 beds

27 Aug – 1 Sept

$1,883 SGD for 5 nights

4.78 out of 5 average rating, 101 reviews

Top guest favourite

Home in Sheffield

Berkshire Getaway~ No Pet Fee! Walk to Distillery

3 bedrooms, 3 beds

5–10 Aug

$2,916 SGD for 5 nights

4.9 out of 5 average rating, 99 reviews

Guest favourite

Home in Sheffield

Water-View Home in the Berkshires

3 bedrooms, 4 beds

23–28 Aug

$2,011 SGD for 5 nights

4.97 out of 5 average rating, 35 reviews

Top guest favourite

Flat in Sheffield

Private Berkshire Barn Apartment

1 bedroom, 1 queen bed

25–30 Sept

$946 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 180 reviews

Top guest favourite

Home in Sheffield

Family friendly house with fenced yard & fire pit

3 bedrooms, 3 beds

16–21 Aug

Free cancellation

4.96 out of 5 average rating, 27 reviews

Top guest favourite

Cottage in Sheffield

The Blue Elm - A Historic Country Cottage

1 bedroom, 2 beds

23–28 Aug

$1,461 SGD for 5 nights

5.0 out of 5 average rating, 95 reviews

Top guest favourite

Home in Sheffield

All new mountain retreat near Great Barrington.

3 bedrooms, 5 beds

4–9 Aug

$4,161 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 7 reviews

Guest favourite

Nature lodge in Sheffield

Sheffield Lodge - Washington Room

1 bedroom, 1 double bed

1–6 Aug

$1,064 SGD for 5 nights

4.93 out of 5 average rating, 46 reviews

Guest favourite

Barn in Sheffield

Modern Dairy Barn

4 bedrooms, 5 beds

7–12 Sept

$3,164 SGD for 5 nights

5.0 out of 5 average rating, 27 reviews

Guest favourite

Home in Sheffield

Berkshires Retreat w/ Pickleball – for Big Groups!

7 bedrooms, 8 beds

2–7 Aug

$5,478 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Superhost

Home in Sheffield

Luxury, Romantic, Timeless Berkshires: Sleeps 18!

8 bedrooms, 11 beds

7–12 Aug

$7,289 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Guest suite in Sheffield

The Sunset Suite~Great South Berkshire Location!

1 queen bed

1–6 Aug

$1,436 SGD for 5 nights

5.0 out of 5 average rating, 93 reviews

Top guest favourite

Home in Sheffield

Beautiful Berkshires Home | Perfect For 3 Families

4 bedrooms, 9 beds

3–8 Aug

$3,950 SGD for 5 nights

4.96 out of 5 average rating, 27 reviews