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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, 97 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
19–24 Jul
Guest favourite
Home in Sheffield
Bull Hill Bungalow
4.98 out of 5 average rating, 51 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
4.79 out of 5 average rating, 100 reviews, 3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
4.96 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4.78 out of 5 average rating, 343 reviews, 4 bedrooms, 8 beds, 3 bathrooms
9–14 Aug
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
4.97 out of 5 average rating, 32 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
4.98 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Barn in Sheffield
Modern Dairy Barn
5.0 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 3 bathrooms
3–8 Sept
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
5.0 out of 5 average rating, 4 reviews, 7 bedrooms, 8 beds, 3.5 bathrooms
12–17 Jul
Guest favourite
Home in Sheffield
Private Berkshires Estate w/ Tennis Court
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 5 beds, 3 bathrooms
29 Jul – 3 Aug
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
4.93 out of 5 average rating, 189 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
5.0 out of 5 average rating, 404 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Sheffield
Belle Meade
4.99 out of 5 average rating, 132 reviews, 2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4.96 out of 5 average rating, 26 reviews, 4 bedrooms, 9 beds, 2 bathrooms
26–31 Jul
Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
4.82 out of 5 average rating, 33 reviews, 5 bedrooms, 7 beds, 2.5 bathrooms
14–19 Aug
Guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
4.97 out of 5 average rating, 29 reviews, 2 bedrooms, 5 beds, 1 bathroom
26–31 Jul
Home in Sheffield
Ashley Falls Home w/ Fire Pit: Hike & Ski!
4.9 out of 5 average rating, 49 reviews, 5 bedrooms, 6 beds, 3 bathrooms
24–29 Aug