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Search results; Over 1,000 homes in Sheffield

Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Greylock Room
1 bedroom, 1 bed, 1 private bathroom
12–17 Jul
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4.92 out of 5 average rating, 77 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
5.0 out of 5 average rating, 404 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Aug
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
4.94 out of 5 average rating, 178 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Home in Sheffield
Perfect Peaceful Berkshire Location !
4.91 out of 5 average rating, 129 reviews, 2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
Guest favourite
Home in Sheffield
Bull Hill Bungalow
4.98 out of 5 average rating, 51 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
Home in Sheffield
Beautiful Berkshires Farmhouse | Escape & Explore
4.6 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
10–15 Jul
Top guest favourite
Room in Sheffield
Sheffield Lodge - Taconic Room
4.98 out of 5 average rating, 54 reviews, 2 single beds, 1 bathroom
12–17 Jul
Guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
4.97 out of 5 average rating, 29 reviews, 2 bedrooms, 5 beds, 1 bathroom
26–31 Jul
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 9 beds, 2.5 bathrooms
19–24 Jul
Top guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
4.96 out of 5 average rating, 178 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Home in Sheffield
House Among Trees - A Perfect Holiday Getaway
4.93 out of 5 average rating, 97 reviews, 3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
Top guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 2 beds, 1 bathroom
9–14 Jul
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
5.0 out of 5 average rating, 4 reviews, 7 bedrooms, 8 beds, 3.5 bathrooms
12–17 Jul
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
5.0 out of 5 average rating, 91 reviews, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
4.96 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Canaan
Cozy Canaan Home near Lime Rock, Newly Renovated
4.98 out of 5 average rating, 41 reviews, 4 bedrooms, 5 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Flat in Canaan
West Main
4.99 out of 5 average rating, 176 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Great Barrington
County Road Hideaway
5.0 out of 5 average rating, 32 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Jul