Sheffield Holidays
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- Plan, book, travel with confidence
- Better togetherSave up to Rp173.195 when you book a flight and hotel together*
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Top hotels in Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
9.8/10 Exceptional! (41 reviews)
The place is lovely, room is cozy, and the bed is comfy
Reviewed on 22 Dec 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is Rp1.563.654 per night from 22 Jan to 23 Jan
Rp1.563.654
Rp1.746.602 total
22 Jan - 23 Jan
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Everything was great!
Reviewed on 8 Jan 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is Rp1.665.507 per night from 1 Feb to 2 Feb
Rp1.665.507
Rp2.237.403 total
1 Feb - 2 Feb
includes taxes & fees
9/10 Wonderful! (810 reviews)
Very comfortable and very close to ski slope and restaurants
Reviewed on 10 Jan 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.
Popular places to visit
Ashley House
You can learn about the history of Sheffield when you stop by Ashley House. Discover the area's breweries or seek out the hiking trails.
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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.
