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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

$1,263 SGD for 5 nights

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5.0 out of 5 average rating, 400 reviews

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms3 beds, 2 bathrooms,

8–13 Jun

$2,420 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,

27 Jul – 1 Aug

$1,173 SGD for 5 nights

4.85 out of 5 average rating, 41 reviews

Top guest favourite

Flat in Sheffield

Private Berkshire Barn Apartment

1 bedroom1 queen bed, 1 bathroom,

4–9 Aug

$959 SGD for 5 nights

4.94 out of 5 average rating, 173 reviews

Guest favourite

Home in Sheffield

Water-View Home in the Berkshires

3 bedrooms4 beds, 2 bathrooms,

23–28 Jun

$2,147 SGD for 5 nights

5.0 out of 5 average rating, 30 reviews

Top guest favourite

Guest suite in Sheffield

The Sunset Suite~Great South Berkshire Location!

1 queen bed1 bathroom,

4–9 Jun

$1,384 SGD for 5 nights

5.0 out of 5 average rating, 89 reviews

Top guest favourite

Home in Salisbury

Greystone at Twin Lakes

3 bedrooms3 beds, 1 bathroom,

5–10 Jun

$1,324 SGD for 5 nights

4.98 out of 5 average rating, 62 reviews

Top guest favourite

Home in Sheffield

Family friendly house with fenced yard & fire pit

3 bedrooms3 beds, 2 bathrooms,

14–19 Jun

$2,746 SGD for 5 nights

4.95 out of 5 average rating, 21 reviews

Guest favourite

Treehouse in New Marlborough

Berkshire Treehouse Retreat

3 bedrooms4 beds, Toilet with sink,

7–12 Jun

$1,702 SGD for 5 nights

4.9 out of 5 average rating, 154 reviews

Top guest favourite

Home in Sheffield

Belle Meade

2 bedrooms2 beds, 2 bathrooms,

8–13 Jun

$2,438 SGD for 5 nights

4.99 out of 5 average rating, 128 reviews

Guest favourite

Home in Great Barrington

4 Mi to Great Barrington: Berkshires Retreat!

3 bedrooms6 beds, 2 bathrooms,

6–11 Jun

$1,395 SGD for 5 nights

5.0 out of 5 average rating, 22 reviews

Top guest favourite

Cottage in Great Barrington

Cottage on Scenic Road

1 bedroom1 queen bed, 1 bathroom,

13–18 Jun

$1,097 SGD for 5 nights

4.91 out of 5 average rating, 271 reviews

Guest favourite

Flat in Great Barrington

County Road Hideaway

1 bedroom1 queen bed, 1 bathroom,

4–9 Jun

$1,611 SGD for 5 nights

5.0 out of 5 average rating, 30 reviews

Top guest favourite

Cottage in Sheffield

The Blue Elm A Historic Country Cottage

1 bedroom2 beds, 1.5 bathrooms,

21–26 Jun

$1,559 SGD for 5 nights

5.0 out of 5 average rating, 87 reviews

Top guest favourite

Home in Sheffield

The Kellogg House in the Heart of The Berkshires

2 bedrooms2 queen beds, 1 bathroom,

21–26 Jun

$2,118 SGD for 5 nights

4.98 out of 5 average rating, 64 reviews

Guest favourite

Cottage in Sheffield

Cheerful 3-bedroom cottage with woodstove.

3 bedrooms4 beds, 2.5 bathrooms,

8–13 Sept

$1,751 SGD for 5 nights

4.93 out of 5 average rating, 182 reviews

Top guest favourite

Guest house in Sheffield

Spring Fling at the Black Bear Bungalow

1 bedroom1 queen bed, 1 bathroom,

4–9 Jun

$1,354 SGD for 5 nights

4.93 out of 5 average rating, 28 reviews

Guest favourite

Home in Sheffield

All new mountain retreat near Great Barrington.

3 bedrooms5 beds, 2 bathrooms,

6–11 Jun

$3,558 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in Sheffield

Perfect Peaceful Berkshire Location !

2 bedrooms2 queen beds, 1 bathroom,

11–16 Sept

$1,362 SGD for 5 nights

4.91 out of 5 average rating, 127 reviews