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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

$1,336 SGD for 5 nights

,

4.98 out of 5 average rating, 57 reviews

Top guest favourite

Flat in Sheffield

Private Berkshire Barn Apartment

1 bedroom, 1 queen bed, 1 bathroom

27 Aug – 1 Sept

$936 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 176 reviews

Home in Sheffield

Beautiful Berkshires Farmhouse | Escape & Explore

4 bedrooms, 5 beds, 4.5 bathrooms

5–10 Jul

$5,570 SGD for 5 nights

4.56 out of 5 average rating, 9 reviews

Top guest favourite

Flat in Sheffield

Hideaway with Spectacular Berkshire Views

1 bedroom, 2 beds, 1 bathroom

24–29 Aug

$1,252 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, 2.5 bathrooms

5–10 Jul

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Home in Sheffield

Family friendly house with fenced yard & fire pit

3 bedrooms, 3 beds, 2 bathrooms

11–16 Jul

Free cancellation

4.96 out of 5 average rating, 23 reviews

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms, 3 beds, 2 bathrooms

6–11 Jul

$2,396 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 50 reviews

Guest favourite

Home in Sheffield

Perfect Peaceful Berkshire Location !

2 bedrooms, 2 queen beds, 1 bathroom

11–16 Sept

$1,374 SGD for 5 nights

4.91 out of 5 average rating, 128 reviews

Top guest favourite

Room in Sheffield

Sheffield Lodge - Taconic Room

2 single beds, 1 bathroom

5–10 Jul

$1,069 SGD for 5 nights

4.98 out of 5 average rating, 54 reviews

Top guest favourite

Home in Sheffield

Great Berkshire Getaway !

1 bedroom, 1 queen bed, 1 bathroom

10–15 Sept

$1,244 SGD for 5 nights

4.95 out of 5 average rating, 111 reviews

Guest favourite

Home in Sheffield

Cozy Cottage Route 7 Sheffield

1 bedroom, 1 bathroom

27 Jul – 1 Aug

$1,189 SGD for 5 nights

4.85 out of 5 average rating, 41 reviews

Guest favourite

Home in Sheffield

Water-View Home in the Berkshires

3 bedrooms, 4 beds, 2 bathrooms

4–9 Jul

$2,210 SGD for 5 nights

4.97 out of 5 average rating, 32 reviews

Guest favourite

Home in Sheffield

Charming Country House with a Hot Tub

4 bedrooms, 5 beds, 2.5 bathrooms

13–18 Jul

$4,044 SGD for 5 nights

4.93 out of 5 average rating, 43 reviews

Top guest favourite

Barn in New Marlborough

Hartsville Barn in the Berkshires

2 bedrooms, 2 king beds, 1 bathroom

14–19 Sept

$1,877 SGD for 5 nights

4.98 out of 5 average rating, 40 reviews

Superhost

Home in Sheffield

Luxury, Romantic, Timeless Berkshires: Sleeps 18!

8 bedrooms, 11 beds, 4.5 bathrooms

7–12 Aug

$7,322 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Guest house in Great Barrington

Berkshires Guest Barn

2 bedrooms, 5 beds, 1 bathroom

12–17 Jul

$1,679 SGD for 5 nights

4.96 out of 5 average rating, 25 reviews

Guest favourite

Home in Sheffield

All new mountain retreat near Great Barrington.

3 bedrooms, 5 beds, 2 bathrooms

7–12 Jul

$4,963 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Loft in Great Barrington

The Old Red Barn

1 bedroom, 1 queen bed, 1 bathroom

1–6 Sept

$1,443 SGD for 5 nights

4.99 out of 5 average rating, 361 reviews

Top guest favourite

Home in Sheffield

Beautiful Berkshires Home | Perfect For 3 Families

4 bedrooms, 9 beds, 2 bathrooms

26–31 Jul

$3,815 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews