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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 - Everett Room
1 bedroom, 2 beds, 1 private bathroom
2–7 Aug
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4.96 out of 5 average rating, 85 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
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
Guest favourite
Home in Sheffield
Renovated, between Butternut and Catamount
4.91 out of 5 average rating, 129 reviews, 2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
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
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
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
5.0 out of 5 average rating, 5 reviews, 7 bedrooms, 8 beds, 3.5 bathrooms
19–24 Jul
Top guest favourite
Home in Sheffield
Mid-century home with sauna and fire pit
4.93 out of 5 average rating, 97 reviews, 3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
Top guest favourite
Flat in Canaan
1890s home with a private garden
4.99 out of 5 average rating, 176 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Home in Sheffield
Secluded 2-acre lot with a hot tub
4.93 out of 5 average rating, 45 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
24–29 Aug
Home in Sheffield
Ashley Falls Home w/ Fire Pit: Hike & Ski!
4.9 out of 5 average rating, 49 reviews, 5 bedrooms, 6 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Guest suite in Sheffield
Hilltop suite with mountain and sunset views
5.0 out of 5 average rating, 92 reviews, 1 bed, 1 bathroom
1–6 Aug
Cabin in Sheffield
Log cabin on a private forest acre
4.78 out of 5 average rating, 344 reviews, 4 bedrooms, 8 beds, 3 bathrooms
9–14 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
Cabin in Mount Washington
10 acres with a pond and fireplace
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 2 beds, 1 bathroom
25–30 Jul
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
4.96 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Sheffield
Scandinavian design with a gym and fire pit
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
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
27 Jul – 1 Aug
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4.96 out of 5 average rating, 27 reviews, 4 bedrooms, 9 beds, 2 bathrooms
26–31 Jul