Sheffield Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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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
9.8/10 Exceptional! (41 reviews)
The place is lovely, room is cozy, and the bed is comfy
Reviewed on Dec 22, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ₩143,992 per night from Feb 1 to Feb 2
₩143,992
₩193,435 total
Feb 1 - Feb 2
includes taxes & fees
9/10 Wonderful! (810 reviews)
Very comfortable and very close to ski slope and restaurants
Reviewed on Jan 10, 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is ₩147,589 per night from Jan 19 to Jan 20
₩147,589
₩164,858 total
Jan 19 - Jan 20
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Everything was great!
Reviewed on Jan 8, 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.
