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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
Aug 24 – 29
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5.0 out of 5 average rating, 407 reviews
Guest favorite
Home in Sheffield
Bull Hill Bungalow
4.98 out of 5 average rating, 52 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 1 – 6
Guest favorite
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 baths
Aug 6 – 11
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4.77 out of 5 average rating, 345 reviews, 4 bedrooms, 8 beds, 3 baths
Aug 9 – 14
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
4.78 out of 5 average rating, 101 reviews, 3 bedrooms, 5 beds, 2 baths
Aug 24 – 29
Top guest favorite
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 baths
Aug 5 – 10
Guest favorite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
4.98 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 2 – 7
Top guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
4.93 out of 5 average rating, 179 reviews, 1 bedroom, 1 bed, 1 bath
Sep 25 – 30
Top guest favorite
Home in Sheffield
Family friendly house with fenced yard & fire pit
4.96 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 16 – 21
Guest favorite
Home in Sheffield
Water-View Home in the Berkshires
4.97 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
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Guesthouse in Sheffield
The Cottage at 3 Sisters Farm
4.83 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 20 – 25
Top guest favorite
Home in Sheffield
All new mountain retreat near Great Barrington.
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 5 beds, 2 baths
Aug 4 – 9
Top guest favorite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
5.0 out of 5 average rating, 95 reviews, 1 bedroom, 2 beds, 1.5 baths
Aug 23 – 28
Guest favorite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
5.0 out of 5 average rating, 6 reviews, 7 bedrooms, 8 beds, 3.5 baths
Aug 2 – 7
Guest favorite
Barn in Sheffield
Modern Dairy Barn
5.0 out of 5 average rating, 27 reviews, 4 bedrooms, 5 beds, 3 baths
Sep 7 – 12
Top guest favorite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 2 beds, 1 bath
Aug 16 – 21
Guest favorite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
4.86 out of 5 average rating, 44 reviews, 1 bedroom, 1 bath
Sep 9 – 14
Top guest favorite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4.96 out of 5 average rating, 27 reviews, 4 bedrooms, 9 beds, 2 baths
Aug 3 – 8
Top guest favorite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
5.0 out of 5 average rating, 92 reviews, 1 bed, 1 bath
Aug 1 – 6