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 €181 per night from 18 Feb to 19 Feb
€181
18 Feb - 19 Feb
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
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield MA
The price is €580 per night from 25 Feb to 26 Feb
€580
25 Feb - 26 Feb
includes taxes & fees
10/10 Exceptional! (9 reviews)
We were a group of moms who snuck away for the night and this cabin was the perfect retreat. Well stocked and very cozy on a winter night. We had to leave very early the next morning to beat a snowstorm and the very long driveway was already sanded and we felt very safe. Lisette was great to work ...
Reviewed on 29 Jan 2026
Antique Farmhouse Totally Restored
Sheffield MA
9.6/10 Exceptional! (62 reviews)
We had a great stay. There is lots of room to spread out for a larger group. The furnishings and decorations are wonderful and eccentric, and the property has a rich history, very tastefully preserved. The kids loved the room with gymnastic rings and feeding the highland cattle across the road. Overall, ...
Reviewed on 27 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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