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Search results; Over 1,000 homes in Sheffield

Top guest favourite
Home in Sheffield
House Among Trees - A Perfect Holiday Getaway
3 bedrooms, 4 beds, 2 private bathrooms
9–14 Sept
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4.93 out of 5 average rating, 97 reviews
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
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
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
5.0 out of 5 average rating, 406 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Aug
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
4.98 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
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
All new mountain retreat near Great Barrington.
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 5 beds, 2 bathrooms
20–25 Jul
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
4.94 out of 5 average rating, 178 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Aug – 1 Sept
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
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
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
4.9 out of 5 average rating, 97 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 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
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
4.97 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
4.78 out of 5 average rating, 101 reviews, 3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
5.0 out of 5 average rating, 94 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
6–11 Aug
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
Home in Great Barrington
Designed for Family Life
New place to stay, 4 bedrooms, 4 beds, 3 bathrooms
1–8 Oct
Top guest favourite
Home in Sheffield
Belle Meade
4.99 out of 5 average rating, 132 reviews, 2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept