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Search results; Over 1,000 homes in Sheffield

Top guest favorite
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, 409 reviews
Guest favorite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 baths
Sep 7 – 12
4.98 out of 5 average rating, 54 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 favorite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 baths
Aug 16 – 21
5.0 out of 5 average rating, 9 reviews
Top guest favorite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds, 2 baths
Aug 9 – 14
4.9 out of 5 average rating, 99 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 baths
Aug 9 – 14
4.77 out of 5 average rating, 347 reviews
Top guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bath
Sep 25 – 30
4.93 out of 5 average rating, 180 reviews
Guest favorite
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, 68 reviews
Guest favorite
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
Top guest favorite
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
Top guest favorite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds, 1.5 baths
Aug 23 – 28
5.0 out of 5 average rating, 96 reviews
Top guest favorite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds, 2 baths
Aug 4 – 9
4.96 out of 5 average rating, 27 reviews
Top guest favorite
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, 7 reviews
Guest favorite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 baths
Sep 7 – 12
5.0 out of 5 average rating, 27 reviews
Guest favorite
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, 7 reviews
Guest favorite
Nature lodge in Sheffield
Sheffield Lodge - Washington Room
1 bedroom, 1 double bed, 1 bath
Aug 9 – 14
4.93 out of 5 average rating, 46 reviews
Guest favorite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom, 1 bath
Sep 9 – 14
4.85 out of 5 average rating, 46 reviews
Top guest favorite
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
Top guest favorite
Home in Sheffield
Belle Meade
2 bedrooms, 2 beds, 2 baths
Sep 21 – 26
4.99 out of 5 average rating, 132 reviews