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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
4 bedrooms, 9 beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 6 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, 50 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 404 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 65 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds, 2 bathrooms
8–13 Jul
5.0 out of 5 average rating, 6 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, 32 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 bathrooms
15–20 Jul
4.78 out of 5 average rating, 342 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
4.79 out of 5 average rating, 100 reviews
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 91 reviews
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bathroom
27 Aug – 1 Sept
4.94 out of 5 average rating, 177 reviews
Top guest favourite
Home in Sheffield
Belle Meade
2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 131 reviews
Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Ramblewood Master
1 bedroom, 1 king bed, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds, 1.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 92 reviews
Top guest favourite
Home in Salisbury
Greystone at Twin Lakes
3 bedrooms, 3 beds, 1 bathroom
31 Jul – 5 Aug
4.98 out of 5 average rating, 66 reviews
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest house in Sheffield
Summer Sizzler at the Black Bear Bungalow
1 bedroom, 1 queen bed, 1 bathroom
25–30 May
4.93 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed, 1 bathroom
26–31 Jul
4.96 out of 5 average rating, 178 reviews