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Search results; Over 1,000 homes in Sheffield

Descriptions are based on details hosts provide
Top guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Monument Room
1 bedroom, 1 bed, 1 private bathroom
31 Aug – 5 Sept
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4.94 out of 5 average rating, 77 reviews
Top guest favourite
Flat in Sheffield
Berkshire views from a secluded hilltop
5.0 out of 5 average rating, 405 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Aug
Guest favourite
Home in Sheffield
Bull Hill Bungalow
4.98 out of 5 average rating, 52 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Sheffield
Across the road from Appalachian Trail
4.98 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 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
Top guest favourite
Home in Sheffield
Cathedral ceilings and a wood stove
4.96 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
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
6–11 Aug
Top guest favourite
Flat in Sheffield
Barn apartment with a private entrance
4.94 out of 5 average rating, 178 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Room in Sheffield
Sheffield Lodge - Taconic Room
4.98 out of 5 average rating, 54 reviews, 2 single beds, 1 bathroom
19–24 Jul
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4.78 out of 5 average rating, 344 reviews, 4 bedrooms, 8 beds, 3 bathrooms
9–14 Aug
Cottage in Sheffield
Handcrafted cottage with a woodstove
4.79 out of 5 average rating, 100 reviews, 3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Cottage in Sheffield
Historic cottage on 3.5 wooded acres
5.0 out of 5 average rating, 94 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
6–11 Aug
Guest favourite
Home in Sheffield
Waterfront with a wood-burning fireplace
4.97 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Sheffield
Private acre overlooking conservation land
4.9 out of 5 average rating, 97 reviews, 3 bedrooms, 3 beds, 2 bathrooms
28 Jul – 2 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 bathroom
1–6 Aug
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
2–7 Aug
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
4.94 out of 5 average rating, 181 reviews, 2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
Guest favourite
Home in Sheffield
Converted church with indoor pickleball court
5.0 out of 5 average rating, 5 reviews, 7 bedrooms, 8 beds, 3.5 bathrooms
19–24 Jul
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
4.93 out of 5 average rating, 190 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Sept