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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
Barn apartment with a private entrance
1 bedroom, 1 queen bed, 1 bathroom
27 Aug – 1 Sept
4.94 out of 5 average rating, 178 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
Renovated, between Butternut and Catamount
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Sept
4.91 out of 5 average rating, 129 reviews
Guest favourite
Home in Sheffield
Five-acre bungalow on a wooded road
3 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Room in Sheffield
Rustic lodge nestled in a pine forest
2 single beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 54 reviews
Guest favourite
Home in Sheffield
Converted church with indoor pickleball court
7 bedrooms, 8 beds, 3.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sheffield
House Among Trees - A Perfect Holiday Getaway
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.93 out of 5 average rating, 97 reviews
Top guest favourite
Flat in Canaan
1890s home with a private garden
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 176 reviews
Top guest favourite
Home in Sheffield
Secluded 2-acre lot with a hot tub
4 bedrooms, 5 beds, 2.5 bathrooms
24–29 Aug
4.93 out of 5 average rating, 45 reviews
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 92 reviews
Cabin in Sheffield
Log cabin on a private forest acre
4 bedrooms, 8 beds, 3 bathrooms
9–14 Aug
4.78 out of 5 average rating, 344 reviews
Home in Sheffield
Game room and fire pit near Berkshires
5 bedrooms, 6 beds, 3 bathrooms
24–29 Aug
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Room in Sheffield
Beautiful Room in Hartfield House - The Berkshires
2 beds, 1 bathroom
27 Jul – 1 Aug
4.97 out of 5 average rating, 37 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
Loft in Great Barrington
Renovated 1830 barn with exposed beams
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.99 out of 5 average rating, 364 reviews
Top guest favourite
Cabin in Mount Washington
10 acres with a pond and fireplace
4 bedrooms, 2 queen beds, 1 bathroom
25–30 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Sheffield
Hot tub, fire pit, and game room
4 bedrooms, 9 beds, 2 bathrooms
26–31 Jul
4.96 out of 5 average rating, 27 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