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Search results; Over 1,000 homes in Sheffield

Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 private bathroom
26 Sept – 1 Oct
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5.0 out of 5 average rating, 408 reviews
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed
25–30 Sept
4.93 out of 5 average rating, 180 reviews
Flat in Sheffield
Historic Kellogg House Apartment - Downstairs
1 bedroom, 1 bed
18–23 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Sheffield
Great Berkshire Getaway !
1 bedroom, 1 queen bed
4–9 Sept
4.95 out of 5 average rating, 113 reviews
Top guest favourite
Room in Sheffield
Sheffield Lodge - Taconic Room
2 single beds
3–8 Aug
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed
1–6 Aug
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds
23–28 Aug
5.0 out of 5 average rating, 95 reviews
Guest favourite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom
9–14 Sept
4.85 out of 5 average rating, 46 reviews
Top guest favourite
Room in Sheffield
Beautiful Room in Hartfield House - The Berkshires
2 beds
9–14 Sept
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed
10–15 Aug
4.99 out of 5 average rating, 365 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
13–18 Sept
4.92 out of 5 average rating, 192 reviews
Guest favourite
Flat in Sheffield
Historic Kellogg House Apartments - Upstairs
2 bedrooms, 2 double beds
12–17 Sept
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Canaan
West Main
2 bedrooms, 2 queen beds
6–11 Sept
4.99 out of 5 average rating, 178 reviews
Top guest favourite
Guest house in Sheffield
Summer Sizzler at the Black Bear Bungalow
1 bedroom, 1 queen bed
25–30 May
4.94 out of 5 average rating, 31 reviews
Home in Great Barrington
Surrounded by nature with a swimming pool
3 bedrooms, 3 beds
15–20 Oct
New place to stay
Top guest favourite
Room in Great Barrington
Cozy & Convenient
1 queen bed
2–7 Aug
5.0 out of 5 average rating, 49 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
7–12 Sept
4.98 out of 5 average rating, 54 reviews
Superhost
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds
9–14 Aug
New place to stay
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed
2–7 Aug
4.89 out of 5 average rating, 66 reviews