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$267 per night from 27 Oct to 28 Oct
S$267
27 Oct - 28 Oct
includes taxes & fees
9.6/10 Exceptional! (33 reviews)
A charming place
"A very charming place to stay. Incredibly quiet with lovely grounds. The trees surround the place are awe inspiring. Owner very friendly and warm. We will stay here again. Very nice breakfast. We are so glad we found this place."
Reviewed on 20 Sept, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is S$164 per night from 28 Sept to 29 Sept
S$164
28 Sept - 29 Sept
includes taxes & fees
8.8/10 Excellent! (655 reviews)
"We like this hotel. Large rooms with good amenities and great location. The hotel shows it's age. Very clean but a little peeling paint and such. One of the people at the reception will need to improve a little. We were told that he os new so hopefully he will learn how to be more welcoming and smile ..."
Reviewed on 24 Sept, 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is S$199 per night from 28 Sept to 29 Sept
S$199
28 Sept - 29 Sept
includes taxes & fees
9/10 Wonderful! (735 reviews)
"The room was fantastic - lots of space and well laid out. Having a kitchen is always very helpful. The property was well kept and clean. I love the rustic vibe. The amenities were awesome - the kids spent all day in the large outdoor pool. We also enjoyed the arcade and mini-golf. The whole area ..."
Reviewed on 22 Sept, 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.
