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 S$243 per night from 12 Jul to 13 Jul
S$243
12 Jul - 13 Jul
includes taxes & fees
9.8/10 Exceptional! (56 reviews)
"Bed was super comfortable. Breakfast was great (love that homemade yogurt) and Laura, the innkeeper, was lovely. Thank you and we can’t wait to come back."
Reviewed on 20 Jun, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is S$230 per night from 6 Jul to 7 Jul
S$230
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"The room was spacious with 2 queen beds. The AC worked well and kept the room cool. We had a glass sliding door to the back of the building that was operational and we could use it to get fresh air or go in and out of. The bathroom was clean and large. The bedding was comfortable and the towels were ..."
Reviewed on 29 Jun, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is S$232 per night from 29 Jul to 30 Jul
S$232
29 Jul - 30 Jul
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"We had a 1 BR suite. It was a large, quiet, clean room. The kitchen and living room had more than we needed. We'll be staying there again."
Reviewed on 29 Jun, 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.
Stay near popular Sheffield attractions
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