Sheffield Holidays
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Your Sheffield Holiday
Our holiday packages to Sheffield allow you to customise your own adventure. Tailor your getaway to your style and interests and make the most of your time in this interesting city. If taking in sights is part of the programme during your trip to Sheffield, stop by leading attractions like Ski Butternut, Housatonic River Walk and Mahaiwe Performing Arts Centre. Stop dreaming and start travelling. Check out the many options on Expedia today and put your Sheffield holiday plans in motion!
Sheffield Holiday
Sheffield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 3,400 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Ski Butternut, Norman Rockwell Museum and Bash Bish Falls State Park |
Our pick of the best Sheffield Hotel Deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
The price is AU$304 per night from 20 Jan to 21 Jan
AU$304
20 Jan - 21 Jan
includes taxes & fees
9.8/10 Exceptional! (42 reviews)
It was a very pleasant hybrid of a classic BnB with the privacy of an air BnB. Host was on point and communicative. We loved hanging out downstairs in the living room(s). Breakfast was fabulous
Reviewed on 14 Jan 2026
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield MA
The price is AU$1,024 per night from 20 Jan to 21 Jan
AU$1,024
20 Jan - 21 Jan
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
Fully refundableReserve now, pay when you stay
The price is AU$198 per night from 1 Feb to 2 Feb
AU$198
1 Feb - 2 Feb
includes taxes & fees
9/10 Wonderful! (813 reviews)
Wonderful night!! Staff go out of their way to help you!!
Reviewed on 17 Jan 2026
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.
