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

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

,

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

Cabin in Sheffield

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

4 bedrooms8 beds, 3 bathrooms,

1–6 Jun

$1,775 SGD for 5 nights

4.78 out of 5 average rating, 340 reviews

Top guest favourite

Home in Sheffield

Belle Meade

2 bedrooms2 beds, 2 bathrooms,

8–13 Jun

$2,427 SGD for 5 nights

4.99 out of 5 average rating, 128 reviews

Top guest favourite

Flat in Sheffield

Private Berkshire Barn Apartment

1 bedroom1 queen bed, 1 bathroom,

4–9 Aug

$958 SGD for 5 nights

4.94 out of 5 average rating, 173 reviews

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms3 beds, 2 bathrooms,

8–13 Jun

$2,409 SGD for 5 nights

4.98 out of 5 average rating, 49 reviews

Guest favourite

Home in Sheffield

Cozy Cottage Route 7 Sheffield

1 bedroom1 bathroom,

8–13 Jun

$1,054 SGD for 5 nights

4.85 out of 5 average rating, 41 reviews

Superhost

Home in Sheffield

Berkshires Retreat w/ Pickleball – for Big Groups!

7 bedrooms8 beds, 3.5 bathrooms,

1–6 Jun

$5,570 SGD for 5 nights

New place to stay

Home in Great Barrington

Downtown Housatonic house –10 miles to Tangelwood

3 bedrooms4 beds, 2 bathrooms,

1–6 Jun

$1,766 SGD for 5 nights

New place to stay

Guest favourite

Home in Sheffield

All new mountain retreat near Great Barrington.

3 bedrooms5 beds, 2 bathrooms,

3–8 Jun

$3,541 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Cabin in Mount Washington

Chic Cabin in the Berkshires, Mountain getaway!

3 bedrooms2 queen beds, 1 bathroom,

11–16 Jul

$2,540 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Superhost

Home in Great Barrington

The Docent's House - Honoring a Legacy

4 bedrooms5 beds, 2 bathrooms,

1–6 Jun

$1,796 SGD for 5 nights

New place to stay

Top guest favourite

Home in Canaan

Cozy Canaan Home near Lime Rock, Newly Renovated

4 bedrooms5 beds, 2 bathrooms,

2–7 Jun

$2,123 SGD for 5 nights

4.97 out of 5 average rating, 39 reviews

Superhost

Home in Sheffield

52-Acre Berkshires Farmhouse • Fire Pit + Trails

4 bedrooms9 beds, 2.5 bathrooms,

7–12 Jun

$2,145 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Cottage in Sheffield

The Blue Elm A Historic Country Cottage

1 bedroom2 beds, 1.5 bathrooms,

21–26 Jun

$1,545 SGD for 5 nights

5.0 out of 5 average rating, 87 reviews

Guest favourite

Flat in Great Barrington

County Road Hideaway

1 bedroom1 queen bed, 1 bathroom,

1–6 Jun

$1,611 SGD for 5 nights

5.0 out of 5 average rating, 30 reviews

Top guest favourite

Flat in Canaan

West Main

2 bedrooms2 queen beds, 1 bathroom,

14–19 Jun

$1,092 SGD for 5 nights

4.99 out of 5 average rating, 173 reviews

Top guest favourite

Cabin in Great Barrington

Modern Luxury Log Cabin

4 bedrooms6 beds, 3 bathrooms,

1–6 Jun

4.96 out of 5 average rating, 110 reviews

Guest favourite

Home in Sheffield

Ashley Falls Home w/ Fire Pit: Hike & Ski!

5 bedrooms6 beds, 3 bathrooms,

27 Jul – 1 Aug

4.93 out of 5 average rating, 46 reviews