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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
Home in Sheffield
Beautiful Berkshires Farmhouse | Escape & Explore
4.6 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
6–11 Jul
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, 177 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
5.0 out of 5 average rating, 6 reviews, 4 bedrooms, 9 beds, 2.5 bathrooms
19–24 Jul
Guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
4.96 out of 5 average rating, 27 reviews, 2 bedrooms, 5 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Sheffield
Bull Hill Bungalow
4.98 out of 5 average rating, 50 reviews, 3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
4.89 out of 5 average rating, 123 reviews, 1 bed, 1 bathroom
5–10 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
Home in Sheffield
Charming Country House with a Hot Tub
4.93 out of 5 average rating, 44 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
5.0 out of 5 average rating, 3 reviews, 7 bedrooms, 8 beds, 3.5 bathrooms
12–17 Jul
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
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
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
5.0 out of 5 average rating, 90 reviews, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Canaan
West Main
4.99 out of 5 average rating, 176 reviews, 2 bedrooms, 2 beds, 1 bathroom
20–25 Aug
Top guest favourite
Home in Sheffield
Great Berkshire Getaway !
4.95 out of 5 average rating, 112 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Sept
Top guest favourite
Home in Great Barrington
The Hideaway: Berkshire Home - village of Egremont
4.95 out of 5 average rating, 144 reviews, 3 bedrooms, 7 beds, 2 bathrooms
9–14 Aug
Guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Top guest favourite
Flat in Great Barrington
County Road Hideaway
5.0 out of 5 average rating, 31 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Jul