Sheffield Holidays
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Top hotels in Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
The price is Rp3.236.197 per night from 3 Mar to 4 Mar
Rp3.236.197
Rp3.614.832 total
3 Mar - 4 Mar
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 23 Jan 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is Rp1.913.467 per night from 3 Mar to 4 Mar
Rp1.913.467
Rp2.512.364 total
3 Mar - 4 Mar
includes taxes & fees
9/10 Wonderful! (866 reviews)
Love it here. We stay a few times a year and are actually local to the hotel. Just a relaxed experience.
Reviewed on 1 Mar 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is Rp1.555.316 per night from 9 Mar to 10 Mar
Rp1.555.316
Rp1.737.288 total
9 Mar - 10 Mar
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
Room is attractive and clean and the staff is always welcoming. Back rooms, where we stay, are quiet and look out across a marsh to the mountain.
Reviewed on 28 Feb 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.
