Search results; Over 1,000 places in Sheffield

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Guest favorite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
8 guests3 bedrooms4 beds2.5 baths
Sep 3 – 8
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Sep 3 – 8
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R24,434 ZAR for 5 nights

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Top guest favorite
Guesthouse in Sheffield
Black Bear Bungalow, Sheffield Mass. U Will Love!
1 queen bed
Jul 20 – 25
R17,851 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
Jul 8 – 13
R13,696 ZAR for 5 nights
4.93 out of 5 average rating, 152 reviews
Top guest favorite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed
Jul 5 – 10
R18,478 ZAR for 5 nights
5.0 out of 5 average rating, 80 reviews
Home in Sheffield
Cozy Cottage Route 7 Sheffield
Aug 24 – 29
R11,400 ZAR for 5 nights
4.81 out of 5 average rating, 27 reviews
Guesthouse in Sheffield
Dandelion Hill Farm Cottage
1 bed
Jul 6 – 11
R11,484 ZAR for 5 nights
New place to stay
Guest favorite
Home in Sheffield
Bull Hill Bungalow
3 beds
Jul 13 – 18
R33,406 ZAR for 5 nights
4.97 out of 5 average rating, 29 reviews
Guest favorite
Home in Sheffield
Majestic Mountain Side FAB. Bardominium Sheffield
5 beds
Aug 31 – Sep 5
R58,355 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Top guest favorite
Home in Salisbury
Greystone at Twin Lakes
3 beds
Aug 6 – 11
R21,401 ZAR for 5 nights
5.0 out of 5 average rating, 50 reviews
Guest favorite
Cabin in Litchfield County
Blackberry Cottage
3 beds
Aug 3 – 8
R19,083 ZAR for 5 nights
4.84 out of 5 average rating, 19 reviews
Guest favorite
Nature lodge in Sheffield
Sheffield Lodge - Ramblewood Master
1 king bed
Jul 6 – 11
R16,181 ZAR for 5 nights
4.98 out of 5 average rating, 47 reviews
Room in Sheffield
Stay with Bradley
Private King bed in vintage BnB
Aug 23 – 28
R20,573 ZAR for 5 nights
Guest favorite
Apartment in Canaan
Private downtown Canaan Apt!
1 king bed
Jul 10 – 15
R20,503 ZAR for 5 nights
5.0 out of 5 average rating, 16 reviews
Guest favorite
Home in Sheffield
Perfect Peaceful Berkshire Location !
2 queen beds
Sep 4 – 9
R18,791 ZAR for 5 nights
4.91 out of 5 average rating, 119 reviews
Home in New Marlborough
Scenic Berkshire retreat near Great Barrington
2 beds
Jul 12 – 17
R27,038 ZAR for 5 nights
Guest favorite
Cabin in Sheffield
Private, peaceful cabin w/ pond in the Berkshires.
4 beds
Jul 24 – 29
R34,449 ZAR for 5 nights
4.95 out of 5 average rating, 20 reviews
Apartment in Great Barrington
Cozy studio near downtown GB
1 bed
Jul 5 – 10
R17,538 ZAR for 5 nights
4.74 out of 5 average rating, 27 reviews
Top guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
2 beds
Sep 15 – 20
R17,121 ZAR for 5 nights
5.0 out of 5 average rating, 367 reviews
Top guest favorite
Home in Canaan
Cozy Canaan Home near Lime Rock, Newly Renovated
3 beds
Jul 27 – Aug 1
R25,681 ZAR for 5 nights
5.0 out of 5 average rating, 22 reviews