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Search results; Over 1,000 homes in Sheffield

Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds, 1.5 private bathrooms
23–28 Aug
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5.0 out of 5 average rating, 95 reviews
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
4.93 out of 5 average rating, 179 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Sept
Flat in Sheffield
Historic Kellogg House Apartment - Downstairs
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
5.0 out of 5 average rating, 408 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Aug
Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Washington Room
4.93 out of 5 average rating, 46 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
4.85 out of 5 average rating, 46 reviews, 1 bedroom, 1 bathroom
9–14 Sept
Top guest favourite
Home in Sheffield
Great Berkshire Getaway !
4.95 out of 5 average rating, 113 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Sept
Superhost
Guest house in Sheffield
The Cottage at 3 Sisters Farm
4.83 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 2 bathrooms
20–25 Aug
Guest favourite
Home in Sheffield
Bull Hill Bungalow
4.98 out of 5 average rating, 54 reviews, 3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Guest house in Sheffield
Summer Sizzler at the Black Bear Bungalow
4.94 out of 5 average rating, 31 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 May
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
5.0 out of 5 average rating, 93 reviews, 1 bed, 1 bathroom
1–6 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 bathroom
27 Aug – 1 Sept
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
4.78 out of 5 average rating, 101 reviews, 3 bedrooms, 5 beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Flat in Great Barrington
Beautfiul, modern, GB apartment
4.81 out of 5 average rating, 301 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Oct
Top guest favourite
Room in Sheffield
Beautiful Room in Hartfield House - The Berkshires
4.97 out of 5 average rating, 37 reviews, 2 beds, 1 bathroom
9–14 Sept
Guest favourite
Flat in Sheffield
Historic Kellogg House Apartments - Upstairs
4.83 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
4.9 out of 5 average rating, 98 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 9 beds, 2.5 bathrooms
16–21 Aug
Superhost
Flat in Great Barrington
Writer/Reader Retreat: Summer or Fall 2026
4.76 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug