Sheffield Holidays
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Sheffield Holiday
Our pick of the best Sheffield Hotel Deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
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 NZ$1,138 per night from 4 Feb to 5 Feb
NZ$1,138
4 Feb - 5 Feb
includes taxes & fees
10/10 Exceptional! (9 reviews)
This was exactly what we were looking for. The property was magnificent the cabin cozy, fully stocked. We plan on coming back soon.
Reviewed on 27 Aug 2025
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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- Charlemont Holidays
- Goose Pond Reservation
- Massachusetts Museum of Contemporary Art
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- Blunt Park
- Ski Butternut
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- Williams College
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- Visit The Berkshires
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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.
