filters

Search results; Over 1,000 homes in Sheffield

Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Washington Room
1 bedroom, 1 bed, 1 shared bathroom
9–14 Jul
,
4.93 out of 5 average rating, 45 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
9–14 Jul
Guest favourite
Home in Sheffield
Bull Hill Bungalow
4.98 out of 5 average rating, 51 reviews, 3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
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
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
Perfect Peaceful Berkshire Location !
4.91 out of 5 average rating, 129 reviews, 2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
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
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
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
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
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
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
5.0 out of 5 average rating, 91 reviews, 1 bed, 1 bathroom
1–6 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
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
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
4.98 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Sheffield
Charming Country House with a Hot Tub
4.93 out of 5 average rating, 45 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4.78 out of 5 average rating, 343 reviews, 4 bedrooms, 8 beds, 3 bathrooms
15–20 Jul