filters

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
,
5.0 out of 5 average rating, 408 reviews
Top guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
4.93 out of 5 average rating, 180 reviews, 1 bedroom, 1 bed, 1 bath
Sep 25 – 30
Apartment in Sheffield
Historic Kellogg House Apartment - Downstairs
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bath
Aug 1 – 6
Guest favorite
Nature lodge in Sheffield
Sheffield Lodge - Washington Room
4.93 out of 5 average rating, 46 reviews, 1 bedroom, 1 bed, 1 bath
Aug 1 – 6
Guest favorite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
4.85 out of 5 average rating, 46 reviews, 1 bedroom, 1 bath
Sep 9 – 14
Top guest favorite
Home in Sheffield
Great Berkshire Getaway !
4.95 out of 5 average rating, 113 reviews, 1 bedroom, 1 bed, 1 bath
Sep 4 – 9
Top guest favorite
Guesthouse in Sheffield
Summer Sizzler at the Black Bear Bungalow
4.94 out of 5 average rating, 31 reviews, 1 bedroom, 1 bed, 1 bath
May 25 – 30
Top guest favorite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
5.0 out of 5 average rating, 93 reviews, 1 bed, 1 bath
Aug 1 – 6
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 27 – Sep 1
Top guest favorite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
4.9 out of 5 average rating, 99 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 5 – 10
Guest favorite
Apartment in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
4.96 out of 5 average rating, 186 reviews, 1 bed, 1 bath
Aug 22 – 27
Guest favorite
Home in Sheffield
Bull Hill Bungalow
4.98 out of 5 average rating, 54 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 7 – 12
Guest favorite
Home in Sheffield
Peaceful and Private Setting
4.95 out of 5 average rating, 37 reviews, 3 bedrooms, 6 beds, 3 baths
Sep 7 – 12
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
Apartment in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
4.89 out of 5 average rating, 65 reviews, 1 bed, 1 bath
Aug 2 – 7
Top guest favorite
Apartment in Canaan
West Main
4.99 out of 5 average rating, 178 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 6 – 11
Guest favorite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
4.99 out of 5 average rating, 67 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 27 – Sep 1
Guest favorite
Apartment in Sheffield
Historic Kellogg House Apartments - Upstairs
4.83 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 12 – 17
Top guest favorite
Room in Sheffield
Beautiful Room in Hartfield House - The Berkshires
4.97 out of 5 average rating, 37 reviews, 2 beds, 1 bath
Sep 9 – 14