Search results; Over 1,000 places in Sheffield

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Guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
2 guests1 bedroom1 bed1 bath
Jul 8 – 13
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Jul 8 – 13
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R15,277 ZAR for 5 nights
for 5 nights

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Top guest favorite
Guesthouse in Sheffield
Black Bear Bungalow, Sheffield Mass. U Will Love!
Free cancellation
Jul 20 – 25
R17,992 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 16 reviews
Home in Sheffield
Cozy Cottage Route 7 Sheffield
Jun 15 – 20
R11,048 ZAR for 5 nights
for 5 nights
4.8 out of 5 average rating, 25 reviews
Guest favorite
Home in Sheffield
Great Berkshire Getaway !
Free cancellation
Nov 6 – 11
R13,993 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 100 reviews
Top guest favorite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed
Jun 11 – 16
R17,571 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 78 reviews
Top guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
2 beds
Jun 12 – 17
R17,108 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 364 reviews
Guest favorite
Home in Sheffield
Perfect Peaceful Berkshire Location !
Free cancellation
Sep 4 – 9
R18,938 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 117 reviews
Superhost
Home in Sheffield
Majestic Mountain Side FAB. Bardominium Sheffield
Free cancellation
Aug 31 – Sep 5
R58,814 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Apartment in Canaan
West Main
2 queen beds
Jun 15 – 20
R12,100 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 143 reviews
Top guest favorite
Home in Salisbury
Greystone at Twin Lakes
Free cancellation
Jul 18 – 23
R21,568 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 49 reviews
Guest favorite
Room in Great Barrington
Stay with KarenWriter, entrepreneur,
Comfy single for a night or two (Eco Airbnb)
Jun 15 – 20
R7,010 ZAR for 5 nights
for 5 nights
4.88 out of 5 average rating, 26 reviews
Top guest favorite
Place to stay in Canaan
Cozy guest rooms in colonial house
Free cancellation
Jul 21 – 26
R21,043 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 14 reviews
Guest favorite
Cabin in Sheffield
Private, peaceful cabin w/ pond in the Berkshires.
Free cancellation
Jun 29 – Jul 4
R35,984 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 20 reviews
Guest favorite
Home in Sheffield
Bull Hill Bungalow
3 beds
Jun 11 – 16
R33,668 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 28 reviews
Room in Sheffield
Stay with Bradley
Private King bed in vintage BnB
Jun 13 – 18
R21,500 ZAR for 5 nights
for 5 nights
Top guest favorite
Nature lodge in Sheffield
Sheffield Lodge - Monument Room
1 queen bed
Jun 14 – 19
R15,277 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 76 reviews
Guest favorite
Cabin in Litchfield County
Blackberry Cottage
Free cancellation
Jul 5 – 10
R18,855 ZAR for 5 nights
for 5 nights
4.8 out of 5 average rating, 10 reviews
Top guest favorite
Room in Great Barrington
Stay with CarolBody, mind, & spirit,
Cozy & Convenient
Jun 15 – 20
R10,521 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 24 reviews
Guest favorite
Apartment in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires
1 bed
Jun 11 – 16
R11,447 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 93 reviews