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Search results; Over 1,000 homes in Sheffield

Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Ramblewood Master
1 bedroom, 1 bed, 1 private bathroom
12–17 Jul
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4.98 out of 5 average rating, 57 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
14–19 Sept
4.98 out of 5 average rating, 51 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds
24–29 Aug
4.79 out of 5 average rating, 100 reviews
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds
19–24 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds
26–31 Jul
4.96 out of 5 average rating, 25 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds
15–20 Jul
4.78 out of 5 average rating, 343 reviews
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds
12–17 Jul
5.0 out of 5 average rating, 3 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, 32 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
2–7 Aug
4.98 out of 5 average rating, 65 reviews
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds
3–8 Sept
5.0 out of 5 average rating, 25 reviews
Home in Sheffield
Ashley Falls Home w/ Fire Pit: Hike & Ski!
5 bedrooms, 6 beds
24–29 Aug
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds
26–31 Jul
4.96 out of 5 average rating, 26 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 4 beds
8–13 Sept
4.93 out of 5 average rating, 189 reviews
Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
5 bedrooms, 7 beds
14–19 Aug
4.82 out of 5 average rating, 33 reviews
Superhost
Home in Sheffield
Luxury, Romantic, Timeless Berkshires: Sleeps 18!
8 bedrooms, 11 beds
7–12 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds
24–29 Aug
5.0 out of 5 average rating, 404 reviews
Top guest favourite
Home in Sheffield
Belle Meade
2 bedrooms, 2 beds
21–26 Sept
4.99 out of 5 average rating, 131 reviews
Top guest favourite
Home in Canaan
Cozy Canaan Home near Lime Rock, Newly Renovated
4 bedrooms, 5 beds
25–30 Jul
4.98 out of 5 average rating, 41 reviews