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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
19–24 Jul
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4.98 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bathroom
27 Aug – 1 Sept
4.94 out of 5 average rating, 178 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 404 reviews
Guest favourite
Home in Sheffield
Perfect Peaceful Berkshire Location !
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Sept
4.91 out of 5 average rating, 129 reviews
Guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
2 bedrooms, 5 beds, 1 bathroom
26–31 Jul
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Room in Sheffield
Sheffield Lodge - Taconic Room
2 single beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 54 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Guest house in Sheffield
Summer Sizzler at the Black Bear Bungalow
1 bedroom, 1 queen bed, 1 bathroom
25–30 May
4.94 out of 5 average rating, 31 reviews
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 4 reviews
Home in Sheffield
Beautiful Berkshires Farmhouse | Escape & Explore
4 bedrooms, 5 beds, 4.5 bathrooms
13–18 Jul
4.6 out of 5 average rating, 10 reviews
Top guest favourite
Home in Sheffield
House Among Trees - A Perfect Holiday Getaway
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.93 out of 5 average rating, 97 reviews
Top guest favourite
Home in Sheffield
Charming Country House with a Hot Tub
4 bedrooms, 5 beds, 2.5 bathrooms
24–29 Aug
4.93 out of 5 average rating, 45 reviews
Top guest favourite
Flat in Canaan
West Main
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 176 reviews
Top guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
4 bedrooms, 2 queen beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Sheffield
Great Berkshire Getaway !
1 bedroom, 1 queen bed, 1 bathroom
4–9 Sept
4.95 out of 5 average rating, 112 reviews
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 bathrooms
6–11 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.99 out of 5 average rating, 364 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 bathrooms
9–14 Aug
4.78 out of 5 average rating, 343 reviews