filters

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
,
4.96 out of 5 average rating, 85 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 405 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 52 reviews
Guest favourite
Home in Sheffield
Across the road from Appalachian Trail
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 65 reviews
Top guest favourite
Home in Sheffield
Scandinavian design with a gym and fire pit
3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 bathrooms
6–11 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bathroom
27 Aug – 1 Sept
4.94 out of 5 average rating, 178 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 bathrooms
9–14 Aug
4.78 out of 5 average rating, 344 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
4.79 out of 5 average rating, 100 reviews
Top guest favourite
Room in Sheffield
Sheffield Lodge - Taconic Room
2 single beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 54 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds, 1.5 bathrooms
6–11 Aug
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Home in Sheffield
Private acre overlooking conservation land
3 bedrooms, 3 beds, 2 bathrooms
28 Jul – 2 Aug
4.9 out of 5 average rating, 97 reviews
Guest favourite
Tiny home in New Marlborough
Secluded among pines with a sauna
2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
4.94 out of 5 average rating, 181 reviews
Superhost
Guest house in Sheffield
Renovated cottage on a Berkshire farm
2 bedrooms, 2 queen beds, 2 bathrooms
2–7 Aug
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Guest suite in Sheffield
Hilltop suite with mountain and sunset views
1 queen bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 92 reviews
Top guest favourite
Barn in New Marlborough
1860s post-and-beam barn with a fire pit
2 bedrooms, 2 king beds, 1 bathroom
14–19 Sept
4.98 out of 5 average rating, 41 reviews
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 5 reviews