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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
,
5.0 out of 5 average rating, 412 reviews
Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds, 4 baths
Sep 8 – 13
New place to stay
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 baths
Sep 7 – 12
4.78 out of 5 average rating, 101 reviews
Top guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bath
Oct 15 – 20
4.93 out of 5 average rating, 182 reviews
Top guest favorite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 baths
Sep 1 – 6
4.96 out of 5 average rating, 28 reviews
Top guest favorite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bath
Sep 14 – 19
4.99 out of 5 average rating, 71 reviews
Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds, 3 baths
Sep 7 – 12
New place to stay
Superhost
Home in Sheffield
New: Heated Pool, SIP, 1 Level Living: Sleeps 10!
3 bedrooms, 7 beds, 3 baths
Sep 7 – 12
New place to stay
Top guest favorite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds, 2 baths
Sep 25 – 30
4.9 out of 5 average rating, 99 reviews
Guest favorite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds, 2 baths
Sep 6 – 11
4.97 out of 5 average rating, 37 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, 55 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 baths
Sep 13 – 18
4.77 out of 5 average rating, 349 reviews
Guest favorite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 baths
Sep 13 – 18
4.92 out of 5 average rating, 192 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
Top guest favorite
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, 97 reviews
Guest favorite
Home in Sheffield
Peaceful and Private Setting
3 bedrooms, 6 beds, 3 baths
Sep 7 – 12
4.95 out of 5 average rating, 38 reviews
Top guest favorite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds, 2 baths
Sep 1 – 6
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 baths
Sep 12 – 17
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom, 1 bath
Sep 9 – 14
4.83 out of 5 average rating, 48 reviews