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Search results; Over 1,000 homes in Sheffield

Top guest favourite
Home in Sheffield
House Among Trees - A Perfect Holiday Getaway
3 bedrooms, 4 beds, 2 private bathrooms
9–14 Sept
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4.93 out of 5 average rating, 98 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
7–12 Sept
4.98 out of 5 average rating, 54 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds
15–20 Aug
4.78 out of 5 average rating, 101 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds
17–22 Aug
4.9 out of 5 average rating, 99 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
27 Aug – 1 Sept
4.99 out of 5 average rating, 68 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds
9–14 Aug
4.77 out of 5 average rating, 347 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds
23–28 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed
25–30 Sept
4.93 out of 5 average rating, 180 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds
16–21 Aug
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 409 reviews
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds
23–28 Aug
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds
19–24 Aug
4.96 out of 5 average rating, 27 reviews
Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Washington Room
1 bedroom, 1 double bed
9–14 Aug
4.93 out of 5 average rating, 46 reviews
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 27 reviews
Superhost
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds
16–21 Aug
New place to stay
Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
5 bedrooms, 7 beds
31 Aug – 5 Sept
4.82 out of 5 average rating, 34 reviews