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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R15,923 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
R18,080 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
R11,102 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
R14,062 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 9 – 14
R17,446 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 77 reviews
Room in Sheffield
Stay with Bradley
Private King bed in vintage BnB
Jun 15 – 20
R16,367 ZAR for 5 nights
for 5 nights
Top guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
2 beds
Jun 9 – 14
R17,128 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 364 reviews
Guest favorite
Apartment in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires
1 bed
Jun 8 – 13
R8,142 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 93 reviews
Guest favorite
Home in Sheffield
Perfect Peaceful Berkshire Location !
Free cancellation
Sep 4 – 9
R19,031 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 117 reviews
Top guest favorite
Home in Canaan
Cozy Canaan Home near Lime Rock, Newly Renovated
3 beds
Jun 9 – 14
R28,990 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 21 reviews
Top guest favorite
Room in Great Barrington
Stay with CarolBody, mind, & spirit,
Cozy & Convenient
Jun 15 – 20
R10,574 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 23 reviews
Top guest favorite
Apartment in Canaan
West Main
2 queen beds
Jun 15 – 20
R12,159 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 143 reviews
Superhost
Home in Sheffield
Majestic Mountain Side FAB. Bardominium Sheffield
Free cancellation
Aug 31 – Sep 5
R59,103 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Apartment in Sheffield
Historic Kellogg House Apartments - Upstairs
2 double beds
Jun 10 – 15
R19,242 ZAR for 5 nights
for 5 nights
4.86 out of 5 average rating, 7 reviews
Top guest favorite
Guesthouse in Great Barrington
Sweet Victorian in Housatonic
6 beds
Jun 8 – 13
R16,388 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 124 reviews
Top guest favorite
Home in Salisbury
Greystone at Twin Lakes
Free cancellation
Jul 18 – 23
R21,674 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 49 reviews
Guest favorite
Nature lodge in Sheffield
Sheffield Lodge - Washington Room
1 double bed
Jun 8 – 13
R13,216 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 41 reviews
Guest favorite
Apartment in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio
1 bed
Jun 8 – 13
R8,142 ZAR for 5 nights
for 5 nights
4.86 out of 5 average rating, 63 reviews
Guest favorite
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
5 beds
Jun 8 – 13
R17,724 ZAR for 5 nights
for 5 nights
4.87 out of 5 average rating, 76 reviews