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Search results; Over 1,000 homes in Sheffield

Nature lodge in Sheffield
Sheffield Lodge
6 bedrooms, 7 beds, 5 private bathrooms
24–29 Aug
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5.0 out of 5 average rating, 14 reviews
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
6–11 Aug
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
5.0 out of 5 average rating, 407 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Aug
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4.77 out of 5 average rating, 345 reviews, 4 bedrooms, 8 beds, 3 bathrooms
9–14 Aug
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
4.78 out of 5 average rating, 101 reviews, 3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
4.9 out of 5 average rating, 97 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
Guest favourite
Home in Sheffield
Bull Hill Bungalow
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
4.98 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
4.93 out of 5 average rating, 179 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Sept
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
4.96 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
4.97 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
5.0 out of 5 average rating, 6 reviews, 7 bedrooms, 8 beds, 3.5 bathrooms
2–7 Aug
Superhost
Home in Sheffield
Luxury, Romantic, Timeless Berkshires: Sleeps 18!
5.0 out of 5 average rating, 3 reviews, 8 bedrooms, 11 beds, 4.5 bathrooms
7–12 Aug
Superhost
Guest house in Sheffield
The Cottage at 3 Sisters Farm
4.83 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 2 bathrooms
20–25 Aug
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 5 beds, 2 bathrooms
4–9 Aug
Guest favourite
Barn in Sheffield
Modern Dairy Barn
5.0 out of 5 average rating, 27 reviews, 4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
5.0 out of 5 average rating, 95 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
23–28 Aug
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4.96 out of 5 average rating, 27 reviews, 4 bedrooms, 9 beds, 2 bathrooms
3–8 Aug
Top guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 2 beds, 1 bathroom
16–21 Aug