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Search results; Over 1,000 homes in Sheffield

Top Guest favourite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 private bath
24–29 Aug
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5.0 out of 5 average rating, 407 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
4.78 out of 5 average rating, 101 reviews, 3 bedrooms, 5 beds, 2 baths
24–29 Aug
Top Guest favourite
Apartment in Sheffield
Private Berkshire Barn Apartment
4.93 out of 5 average rating, 179 reviews, 1 bedroom, 1 bed, 1 bath
25–30 Sept
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4.77 out of 5 average rating, 345 reviews, 4 bedrooms, 8 beds, 3 baths
9–14 Aug
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 baths
6–11 Aug
Guest favourite
Home in Sheffield
Bull Hill Bungalow
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 2 baths
1–6 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 baths
5–10 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 baths
23–28 Aug
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
4.99 out of 5 average rating, 67 reviews, 2 bedrooms, 2 beds, 1 bath
27 Aug – 1 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 baths
16–21 Aug
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 baths
23–28 Aug
Guest favourite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
4.86 out of 5 average rating, 44 reviews, 1 bedroom, 1 bath
9–14 Sept
Superhost
Guesthouse in Sheffield
The Cottage at 3 Sisters Farm
4.83 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 2 baths
20–25 Aug
Top Guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
5.0 out of 5 average rating, 92 reviews, 1 bed, 1 bath
1–6 Aug
Guest favourite
Barn in Sheffield
Modern Dairy Barn
5.0 out of 5 average rating, 27 reviews, 4 bedrooms, 5 beds, 3 baths
7–12 Sept
Top Guest favourite
Guesthouse in Sheffield
Summer Sizzler at the Black Bear Bungalow
4.94 out of 5 average rating, 31 reviews, 1 bedroom, 1 bed, 1 bath
25–30 May
Top Guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
4.98 out of 5 average rating, 42 reviews, 2 bedrooms, 2 beds, 1 bath
14–19 Sept
Guest favourite
Home in Sheffield
Perfect Peaceful Berkshire Location !
4.91 out of 5 average rating, 129 reviews, 2 bedrooms, 2 beds, 1 bath
11–16 Sept
Top Guest favourite
Home in Sheffield
Great Berkshire Getaway !
4.95 out of 5 average rating, 113 reviews, 1 bedroom, 1 bed, 1 bath
4–9 Sept
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