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$232 per night from 30 Dec to 31 Dec
S$232
30 Dec - 31 Dec
includes taxes & fees
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 S$133 per night from 4 Jan to 5 Jan
S$133
4 Jan - 5 Jan, 2026
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
The bed was very comfortable. The staff was helpful and courteous
Reviewed on 24 Dec, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is S$170 per night from 11 Jan to 12 Jan
S$170
11 Jan - 12 Jan, 2026
includes taxes & fees
9/10 Wonderful! (796 reviews)
Clean and warm, very spacious and cozy. People here are very nice too! Very good experience here.
Reviewed on 26 Dec, 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.
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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. 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.
