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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

$1,334 SGD for 5 nights

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4.98 out of 5 average rating, 57 reviews

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms, 3 beds, 2 bathrooms

6–11 Jul

$2,347 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 50 reviews

Guest favourite

Home in Sheffield

52-Acre Berkshires Farmhouse • Fire Pit + Trails

4 bedrooms, 9 beds, 2.5 bathrooms

5–10 Jul

$2,970 SGD for 5 nights

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

Water-View Home in the Berkshires

3 bedrooms, 4 beds, 2 bathrooms

4–9 Jul

$2,207 SGD for 5 nights

4.97 out of 5 average rating, 32 reviews

Cabin in Sheffield

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

4 bedrooms, 8 beds, 3 bathrooms

15–20 Jul

4.78 out of 5 average rating, 341 reviews

Top guest favourite

Home in Sheffield

All new mountain retreat near Great Barrington.

3 bedrooms, 5 beds, 2 bathrooms

7–12 Jul

$4,956 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 6 reviews

Guest favourite

Barn in Sheffield

Modern Dairy Barn

4 bedrooms, 5 beds, 3 bathrooms

3–8 Sept

$4,130 SGD for 5 nights

5.0 out of 5 average rating, 25 reviews

Superhost

Home in Sheffield

Luxury, Romantic, Timeless Berkshires: Sleeps 18!

8 bedrooms, 11 beds, 4.5 bathrooms

7–12 Aug

$7,311 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Sheffield

Beautiful Berkshires Home | Perfect For 3 Families

4 bedrooms, 9 beds, 2 bathrooms

26–31 Jul

$3,810 SGD for 5 nights

4.96 out of 5 average rating, 26 reviews

Guest favourite

Home in Sheffield

The Kellogg House in the Heart of The Berkshires

2 bedrooms, 2 queen beds, 1 bathroom

5–10 Jul

$2,134 SGD for 5 nights

4.98 out of 5 average rating, 65 reviews

Top guest favourite

Flat in Sheffield

Hideaway with Spectacular Berkshire Views

1 bedroom, 2 beds, 1 bathroom

24–29 Aug

$1,250 SGD for 5 nights

5.0 out of 5 average rating, 404 reviews

Top guest favourite

Home in Sheffield

Belle Meade

2 bedrooms, 2 beds, 2 bathrooms

21–26 Sept

$2,457 SGD for 5 nights

4.99 out of 5 average rating, 131 reviews

Home in Sheffield

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

5 bedrooms, 6 beds, 3 bathrooms

24–29 Aug

4.9 out of 5 average rating, 49 reviews

Guest favourite

Home in Sheffield

Serene Berkshire Artist's House

3 bedrooms, 3 beds, 2.5 bathrooms

6–11 Jul

$2,972 SGD for 5 nights

4.99 out of 5 average rating, 69 reviews

Guest favourite

Cottage in Sheffield

Cheerful 3-bedroom cottage with woodstove.

3 bedrooms, 4 beds, 2.5 bathrooms

8–13 Sept

$1,743 SGD for 5 nights

4.93 out of 5 average rating, 188 reviews

Top guest favourite

Flat in Sheffield

Private Berkshire Barn Apartment

1 bedroom, 1 queen bed, 1 bathroom

27 Aug – 1 Sept

$935 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 177 reviews

Guest favourite

Home in Sheffield

Perfect Peaceful Berkshire Location !

2 bedrooms, 2 queen beds, 1 bathroom

11–16 Sept

$1,372 SGD for 5 nights

4.91 out of 5 average rating, 128 reviews

Guest favourite

Treehouse in New Marlborough

Berkshire Treehouse Retreat

3 bedrooms, 4 beds, Toilet with sink

12–17 Jul

$1,715 SGD for 5 nights

4.9 out of 5 average rating, 157 reviews