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Search results; Over 1,000 homes in Sheffield

Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Greylock Room
1 bedroom, 1 bed, 1 private bathroom
12–17 Jul
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4.92 out of 5 average rating, 77 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
14–19 Sept
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
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
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
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
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
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
15–20 Jul
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
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
5.0 out of 5 average rating, 91 reviews, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
4.94 out of 5 average rating, 177 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Home in Sheffield
Belle Meade
4.99 out of 5 average rating, 131 reviews, 2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept
Top guest favourite
Home in Salisbury
Greystone at Twin Lakes
4.98 out of 5 average rating, 66 reviews, 3 bedrooms, 3 beds, 1 bathroom
31 Jul – 5 Aug
Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Ramblewood Master
4.98 out of 5 average rating, 57 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
5.0 out of 5 average rating, 3 reviews, 7 bedrooms, 8 beds, 3.5 bathrooms
12–17 Jul
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
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
4.98 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
4.94 out of 5 average rating, 177 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Jul – 2 Aug