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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
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
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
Home in Sheffield
Belle Meade
2 bedrooms2 beds, 2 bathrooms,
8–13 Jun
4.99 out of 5 average rating, 128 reviews
Guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms5 beds, 2 bathrooms,
24–29 Jun
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom1 bathroom,
27 Jul – 1 Aug
4.85 out of 5 average rating, 41 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
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
Superhost
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms9 beds, 2.5 bathrooms,
21–26 Jun
5.0 out of 5 average rating, 4 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms8 beds, 3 bathrooms,
20–25 Jun
4.78 out of 5 average rating, 340 reviews
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed1 bathroom,
5–10 Jun
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Home in Salisbury
Greystone at Twin Lakes
3 bedrooms3 beds, 1 bathroom,
27 Jun – 2 Jul
4.98 out of 5 average rating, 62 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
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms3 beds, 2 bathrooms,
7–12 Jun
4.89 out of 5 average rating, 94 reviews
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms4 beds, 2 bathrooms,
9–14 Jun
New place to stay
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms5 beds, 3 bathrooms,
6–11 Jun
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in New Marlborough
Scenic Berkshire retreat near Great Barrington
2 bedrooms2 beds, 1 bathroom,
6–11 Jun
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Great Barrington
4 Mi to Great Barrington: Berkshires Retreat!
3 bedrooms6 beds, 2 bathrooms,
7–12 Jun
5.0 out of 5 average rating, 22 reviews