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$328 per night from 22 June to 23 June
NZ$328
22 June - 23 June
includes taxes & fees
9.8/10 Exceptional! (54 reviews)
"The welcoming spaces still allowed for privacy while providing the most wonderful comforts such as cold and hot drinks, books,board games and a garden retreat. Our room could be kept at our preferred temperature with an individual, quiet cooling unit that didn't block the garden view. The morning ..."
Reviewed on 10 June 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$311 per night from 19 July to 20 July
NZ$311
19 July - 20 July
includes taxes & fees
9/10 Wonderful! (988 reviews)
"The room seemed clean it was nice to have the separate living room and kitchen area with a tv available on each living space . When I went to bed and pulled comforter a large amount of dust hit me in the face. I started coughing . The inner sheets were clean but the comforter was worn and dusty Overall ..."
Reviewed on 18 June 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$247 per night from 21 June to 22 June
NZ$247
21 June - 22 June
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"A great hotel to stay in Berkshires. Close to everything we wanted: trails, cafes and restaurants, places of interest. Comfortable room again with everything we need in it. Amazing complex of in and outdoors pools, exercise room, hot tub, a decent breakfast. And an uncomparable per night price."
Reviewed on 19 June 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.
Stay near popular Sheffield attractions
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.
