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$197 per night from 16 Nov to 17 Nov
S$197
16 Nov - 17 Nov
includes taxes & fees
9.6/10 Exceptional! (38 reviews)
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!
Reviewed on 10 Nov, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (750 reviews)
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.
Reviewed on 4 Nov, 2025
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 16 Nov to 17 Nov
S$135
16 Nov - 17 Nov
includes taxes & fees
9/10 Wonderful! (796 reviews)
Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere.
Reviewed on 10 Nov, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
