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Search results; Over 1,000 homes in Sheffield

Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Ramblewood Master
1 bedroom, 1 bed, 1 private bathroom
5–10 Jul
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4.98 out of 5 average rating, 57 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, 176 reviews
Guest favourite
Home in Sheffield
Beautiful Berkshires Farmhouse | Escape & Explore
4 bedrooms, 5 beds, 4.5 bathrooms
5–12 Jul
4.56 out of 5 average rating, 9 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 bathrooms
15–20 Jul
4.78 out of 5 average rating, 341 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, 403 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
4.98 out of 5 average rating, 50 reviews
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
4–9 Jul
New place to stay
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom, 1 bathroom
27 Jul – 1 Aug
4.85 out of 5 average rating, 41 reviews
Top guest favourite
Room in Sheffield
Sheffield Lodge - Taconic Room
2 single beds, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 53 reviews
Guest favourite
Home in Sheffield
Perfect Peaceful Berkshire Location !
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Sept
4.91 out of 5 average rating, 128 reviews
Top guest favourite
Home in Sheffield
Great Berkshire Getaway !
1 bedroom, 1 queen bed, 1 bathroom
10–15 Sept
4.95 out of 5 average rating, 111 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
Flat in Canaan
West Main
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Jul
4.99 out of 5 average rating, 175 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds, 2 bathrooms
4–9 Jul
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
6–11 Jul
4.99 out of 5 average rating, 360 reviews
Guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
2 bedrooms, 5 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 39 reviews