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Search results; Over 1,000 homes in Sheffield

Top guest favourite
Guest house in Sheffield
Summer Sizzler at the Black Bear Bungalow
1 bedroom, 1 bed, 1 private bathroom
27 Aug – 1 Sept
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4.94 out of 5 average rating, 31 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.78 out of 5 average rating, 101 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 55 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in Sheffield
Serene Berkshire Artist's House
3 bedrooms, 3 beds, 2.5 bathrooms
7–12 Sept
4.99 out of 5 average rating, 69 reviews
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 72 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 192 reviews
Guest favourite
Home in Sheffield
Private Berkshires Estate w/ Tennis Court
4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
4.98 out of 5 average rating, 40 reviews
Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds, 4 bathrooms
8–13 Sept
New place to stay
Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
New place to stay
Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
5 bedrooms, 7 beds, 2.5 bathrooms
31 Oct – 5 Nov
4.83 out of 5 average rating, 35 reviews
Top guest favourite
Home in Sheffield
Belle Meade
2 bedrooms, 2 beds, 2 bathrooms
8–13 Dec
4.99 out of 5 average rating, 133 reviews
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bathroom
4–9 Nov
4.93 out of 5 average rating, 183 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
4.77 out of 5 average rating, 351 reviews
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 9 reviews