Sheffield Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
The price is NZ$350 per night from 7 May to 8 May
NZ$350
7 May - 8 May
includes taxes & fees
9.8/10 Exceptional! (46 reviews)
Loved everything!
Reviewed on 27 Apr 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$204 per night from 24 May to 25 May
NZ$204
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (923 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on 4 May 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$183 per night from 7 May to 8 May
NZ$183
7 May - 8 May
includes taxes & fees
9/10 Wonderful! (930 reviews)
This is a very nice, quasi-boutique hotel. The rooms are nicely furnished but small. It is not fancy but it is comfortable, clean, and perfectly fine…just not fancy. But I’m not a fancy person so I like this place and will stay again without hesitation. The only reason for a 4-star rating is that, ...
Reviewed on 4 May 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.
Explore a world of travel with Expedia
- Resort in Hinsdale
- B&B in Great Barrington
- B&B in Ashuwillticook Rail Trail
- B&B in The Berkshires
- Resort in The Berkshires
- Cabin Rentals in The Berkshires
- Apartments in Southwick
- Apartments in Westfield
- Cottages in Mill River
- Motels in Becket
- Condo Rentals in Otis
- Apartments in Granville
- Resort in Granville
- B&B in Granville
- B&B in Lenox
- Cottages in Lenox
- Apartments in Lanesborough
- Cottages in Southfield
- Lenox Hotels
- Lanesborough Hotels
- Great Barrington Hotels
- Stockbridge Hotels
- Peru Hotels
- Washington Hotels
- Becket Hotels
- Hotels near Berkshire Museum
- Hotels near Magnolia Bluffs Casino
- Chester Hotels
- Mount Washington Hotels
- Blandford Hotels
- Hotels near Tanglewood Music Center
- Pittsfield Hotels
- Hotels near Walter J. Koladza
- Sheffield Hotels
- Granville Hotels
- Hotels near Lake Mansfield Park
- New Marlborough Hotels
- Hotels near Jiminy Peak Mountain Resort
- South Egremont Hotels
- Russell Hotels
- Alford Hotels
- Tyringham Hotels
- Richmond Hotels
- Lee Hotels
- Huntington Hotels
- Monterey Hotels
- Otis Hotels
- Dalton Hotels
- Berkshire County Hotels
- West Stockbridge Hotels
- Hancock Hotels
- Hotels near Guido's Marketplace
- Westfield Hotels
- Hotels near Ashintully Gardens
- Cheshire Hotels
- Southwick Hotels
- Accor Hotels in Russell
- Lgbt Welcoming Hotels in Lee
- Beach Hotels in Lee
- Cheap Hotels in Lenox
- Luxury Hotels in The Berkshires
- Golf Hotels in The Berkshires
- Hotels with Pool in Sheffield
- Charlemont Holidays
- Goose Pond Reservation
- Massachusetts Museum of Contemporary Art
- Otis Holidays
- Springfield Armory
- Pittsfield Holidays
- Chicopee Holidays
- Blunt Park
- Ski Butternut
- North Adams Holidays
- National Shrine of the Divine Mercy
- Sterling and Francine Clark Art Institute
- Cheshire Holidays
- Williams College
- Norman Rockwell Museum
- Hadley Farm Museum
- Visit The Berkshires
- Visit Great Barrington
- Visit West Stockbridge
- Visit Middlefield
- Visit Tyringham
- Visit Otis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
