Sheffield Holidays
- Plan, book, travel with confidence
Better together
Save up to €185 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top hotels in Sheffield
Wilder House Berkshires
48 S Main Street, Sheffield, MA
The price is €191 per night from 1 Oct to 2 Oct
€191
1 Oct - 2 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
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
The price is €604 per night from 24 Sept to 25 Sept
€604
24 Sept - 25 Sept
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
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is €94 per night from 24 Sept to 25 Sept
€94
24 Sept - 25 Sept
includes taxes & fees
8.8/10 Excellent! (653 reviews)
"It was a great Stay where we had to it was a good area I would come back to this place again"
Reviewed on 21 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.
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
