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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
,
5.0 out of 5 average rating, 400 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
Belle Meade
2 bedrooms2 beds, 2 bathrooms,
8–13 Jun
4.99 out of 5 average rating, 128 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
Cozy Cottage Route 7 Sheffield
1 bedroom1 bathroom,
27 Jul – 1 Aug
4.85 out of 5 average rating, 41 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
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
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
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
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
3 bedrooms2 queen beds, 1 bathroom,
11–16 Jul
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms8 beds, 3.5 bathrooms,
5–10 Jun
New place to stay
Guest favourite
Home in Sheffield
Ashley Falls Home w/ Fire Pit: Hike & Ski!
5 bedrooms6 beds, 3 bathrooms,
27 Jul – 1 Aug
4.94 out of 5 average rating, 47 reviews
Guest favourite
Home in Sheffield
Beautiful Berkshires Farmhouse | Escape & Explore
4 bedrooms5 beds, 4.5 bathrooms,
14–19 Jun
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Great Barrington
The Docent's House - Honoring a Legacy
4 bedrooms5 beds, 2 bathrooms,
5–10 Jun
New place to stay
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4 bedrooms6 beds, 3 bathrooms,
7–12 Jun
4.96 out of 5 average rating, 110 reviews
Guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed1 bathroom,
22–27 Jun
4.91 out of 5 average rating, 189 reviews
Guest favourite
Home in Sheffield
Peaceful and Private Setting
3 bedrooms6 beds, 3 bathrooms,
26–31 Jul
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Home in Canaan
Cozy Canaan Home near Lime Rock, Newly Renovated
4 bedrooms5 beds, 2 bathrooms,
6–11 Jun
4.98 out of 5 average rating, 40 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms2 beds, 1 bathroom,
28 Jun – 3 Jul
4.94 out of 5 average rating, 168 reviews