Sheffield Vacations
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- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
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Find the Best Sheffield Vacation Packages
Sheffield Hotel Deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
The price is ₩274,762 per night from Mar 1 to Mar 2
₩274,762
₩306,908 total
Mar 1 - Mar 2
includes taxes & fees
9.8/10 Exceptional! (43 reviews)
Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back.
Reviewed on Jan 23, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ₩162,458 per night from Mar 1 to Mar 2
₩162,458
₩213,306 total
Mar 1 - Mar 2
includes taxes & fees
9/10 Wonderful! (864 reviews)
Overcharged and lied to said security deposit was released back but never was
Reviewed on Feb 26, 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is ₩132,050 per night from Mar 8 to Mar 9
₩132,050
₩147,500 total
Mar 8 - Mar 9
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Yrs
Reviewed on Feb 23, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
