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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
24–29 Aug
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5.0 out of 5 average rating, 407 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
24–29 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, 2.5 bathrooms
6–11 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bathroom
25–30 Sept
4.93 out of 5 average rating, 179 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 bathrooms
9–14 Aug
4.77 out of 5 average rating, 346 reviews
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
4.9 out of 5 average rating, 98 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
27 Aug – 1 Sept
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 26 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.97 out of 5 average rating, 35 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
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds, 1.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds, 2 bathrooms
4–9 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds, 2 bathrooms
3–8 Aug
4.96 out of 5 average rating, 27 reviews
Guest favourite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom, 1 bathroom
9–14 Sept
4.86 out of 5 average rating, 44 reviews
Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
5 bedrooms, 7 beds, 2.5 bathrooms
31 Aug – 5 Sept
4.82 out of 5 average rating, 34 reviews
Superhost
Guest house in Sheffield
The Cottage at 3 Sisters Farm
2 bedrooms, 2 queen beds, 2 bathrooms
20–25 Aug
4.83 out of 5 average rating, 12 reviews
Superhost
Home in Sheffield
Luxury, Romantic, Timeless Berkshires: Sleeps 18!
8 bedrooms, 11 beds, 4.5 bathrooms
7–12 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 6 reviews