Search results; Over 1,000 places in Sheffield

The home you selected

Guest favorite
Home in Sheffield
Deck, River Views, Mini Gym, Sleeps 8
11 guests4 bedrooms4 beds2.5 baths
Mar 1 – 6
More
Mar 1 – 6
More
R46,394 ZAR for 5 nights

Explore more homes

Home in Sheffield
Charming Berkshires Cottage Retreat
4 beds
Jul 19 – 24
R30,556 ZAR for 5 nights
New place to stay
Top guest favorite
Guesthouse in Sheffield
Black Bear Bungalow, Sheffield Mass. U Will Love!
1 queen bed
Jul 20 – 25
R18,238 ZAR for 5 nights
5.0 out of 5 average rating, 17 reviews
Top guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
1 queen bed
Aug 19 – 24
R16,105 ZAR for 5 nights
4.93 out of 5 average rating, 153 reviews
Top guest favorite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed
Jul 30 – Aug 4
R18,878 ZAR for 5 nights
5.0 out of 5 average rating, 81 reviews
Superhost
Home in Sheffield
Cozy Cottage Route 7 Sheffield
Aug 24 – 29
R11,476 ZAR for 5 nights
4.82 out of 5 average rating, 28 reviews
Guest favorite
Home in Sheffield
Majestic Mountain Side FAB. Bardominium Sheffield
5 beds
Aug 31 – Sep 5
R59,619 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Sheffield
Perfect Peaceful Berkshire Location !
2 queen beds
Sep 4 – 9
R19,198 ZAR for 5 nights
4.91 out of 5 average rating, 119 reviews
Guesthouse in Sheffield
Dandelion Hill Farm Cottage
1 bed
Jul 18 – 23
R11,732 ZAR for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Sheffield
Bull Hill Bungalow
3 beds
Jul 14 – 19
R34,129 ZAR for 5 nights
4.97 out of 5 average rating, 30 reviews
Top guest favorite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
2 beds
Jul 20 – 25
R23,912 ZAR for 5 nights
5.0 out of 5 average rating, 71 reviews
Top guest favorite
Home in Sheffield
Belle Meade
2 beds
Sep 10 – 15
R45,861 ZAR for 5 nights
4.99 out of 5 average rating, 109 reviews
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 king beds
Aug 1 – 6
R23,464 ZAR for 5 nights
New place to stay
Top guest favorite
Room in Sheffield
Stay with SusanIndoor designer,
Sheffield Lodge - Taconic Room
Aug 31 – Sep 5
R13,866 ZAR for 5 nights
4.98 out of 5 average rating, 51 reviews
Guest favorite
Home in Great Barrington
Berkshires Black Abbey
4 beds
Aug 10 – 15
R48,954 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Guest favorite
Apartment in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 bed
Jul 20 – 25
R9,194 ZAR for 5 nights
4.85 out of 5 average rating, 39 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
8 beds
Aug 4 – 9
R40,072 ZAR for 5 nights
4.8 out of 5 average rating, 304 reviews
Room in Sheffield
Stay with Bradley
Private King bed in vintage BnB
Jul 27 – Aug 1
R19,913 ZAR for 5 nights
Guest favorite
Cabin in Sheffield
Private, peaceful cabin w/ pond in the Berkshires.
4 beds
Jul 20 – 25
R34,812 ZAR for 5 nights
4.95 out of 5 average rating, 21 reviews