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Search results; Over 1,000 homes in Sheffield

Top guest favourite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 private bath
Sep 26–Oct 1
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5.0 out of 5 average rating, 410 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 baths
Aug 27–Sep 1
4.78 out of 5 average rating, 101 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 baths
Sep 7–12
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bath
Aug 27–Sep 1
4.99 out of 5 average rating, 69 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 baths
Aug 23–28
4.77 out of 5 average rating, 348 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 baths
Aug 23–28
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds, 1.5 baths
Sep 21–26
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds, 2 baths
Aug 17–22
4.9 out of 5 average rating, 99 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 baths
Aug 16–21
4.96 out of 5 average rating, 27 reviews
Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
5 bedrooms, 7 beds, 2.5 baths
Aug 31–Sep 5
4.82 out of 5 average rating, 34 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 baths
Aug 16–21
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed, 1 bath
Aug 23–28
5.0 out of 5 average rating, 95 reviews
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 baths
Sep 7–12
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Sheffield
Great Berkshire Getaway !
1 bedroom, 1 queen bed, 1 bath
Sep 4–9
4.95 out of 5 average rating, 115 reviews
Guest favourite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom, 1 bath
Sep 9–14
4.83 out of 5 average rating, 47 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds, 2 baths
Aug 23–28
4.97 out of 5 average rating, 36 reviews
Guest favourite
Guesthouse in Sheffield
Dandelion Hill Farm Cottage
1 bedroom, 1 bed, 1 bath
Aug 16–21
4.85 out of 5 average rating, 26 reviews
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds, 2 baths
Aug 28–Sep 2
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bath
Oct 15–20
4.93 out of 5 average rating, 181 reviews