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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
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5.0 out of 5 average rating, 400 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
4.98 out of 5 average rating, 64 reviews
Guest favourite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom1 bathroom,
8–13 Jun
4.85 out of 5 average rating, 41 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms3 beds, 2 bathrooms,
8–13 Jun
4.98 out of 5 average rating, 49 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms4 beds, 2 bathrooms,
23–28 Jun
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms5 beds, 2 bathrooms,
5–10 Jun
5.0 out of 5 average rating, 5 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms8 beds, 3 bathrooms,
7–12 Jun
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
4.99 out of 5 average rating, 128 reviews
Guest favourite
Guest house in Sheffield
Dandelion Hill Farm Cottage
1 bedroom1 bed, 1 bathroom,
7–12 Jun
4.9 out of 5 average rating, 21 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms3 beds, 2 bathrooms,
14–19 Jun
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom1 queen bed, 1 bathroom,
4–9 Aug
4.94 out of 5 average rating, 173 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms2 beds, 1 bathroom,
13–18 Jun
4.94 out of 5 average rating, 168 reviews
Superhost
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms9 beds, 2.5 bathrooms,
7–12 Jun
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed1 bathroom,
3–8 Jun
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Guest house in Sheffield
Spring Fling at the Black Bear Bungalow
1 bedroom1 queen bed, 1 bathroom,
3–8 Jun
4.93 out of 5 average rating, 28 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms4 beds, 2.5 bathrooms,
8–13 Sept
4.93 out of 5 average rating, 182 reviews
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms4 beds, 2 bathrooms,
3–8 Jun
New place to stay
Guest favourite
Home in Sheffield
Great Berkshire Getaway !
1 bedroom1 queen bed, 1 bathroom,
4–9 Sept
4.95 out of 5 average rating, 110 reviews
Guest favourite
Flat in Great Barrington
County Road Hideaway
1 bedroom1 queen bed, 1 bathroom,
3–8 Jun
5.0 out of 5 average rating, 30 reviews