Pittsfield Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 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
Pittsfield Holiday
Our pick of the best Pittsfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$230 per night from 1 Feb to 2 Feb
NZ$230
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
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is NZ$190 per night from 23 Jan to 24 Jan
NZ$190
23 Jan - 24 Jan
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Staff was very courteous and rooms clean.
Reviewed on 12 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$183 per night from 25 Jan to 26 Jan
NZ$183
25 Jan - 26 Jan
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Very clean...i dotted and t crossed
Reviewed on 16 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.
Explore a world of travel with Expedia
- Resort in Hinsdale
- Motels in New Ashford
- 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 Williamstown
- B&B in Adams
- Motels in Becket
- Condo Rentals in Otis
- B&B in Lenox
- Cottages in Lenox
- Lodges in Cheshire
- Cabin Rentals in Cheshire
- Apartments in Lanesborough
- Lenox Hotels
- Lanesborough Hotels
- Savoy Hotels
- Great Barrington Hotels
- Stockbridge Hotels
- Peru Hotels
- Washington Hotels
- Becket Hotels
- Hotels near Berkshire Museum
- Chester Hotels
- Plainfield Hotels
- Hotels near Tanglewood Music Center
- Pittsfield Hotels
- Florida Hotels
- Hotels near Walter J. Koladza
- Windsor Hotels
- North Adams Hotels
- Hotels near Lake Mansfield Park
- Hotels near Jiminy Peak Mountain Resort
- Cummington Hotels
- Drury Hotels
- Alford Hotels
- Tyringham Hotels
- Richmond Hotels
- Lee Hotels
- Monterey Hotels
- New Ashford Hotels
- Otis Hotels
- Dalton Hotels
- Berkshire County Hotels
- West Stockbridge Hotels
- Hancock Hotels
- Hotels near Guido's Marketplace
- Hotels near Ashintully Gardens
- Cheshire Hotels
- Williamstown Hotels
- Adams Hotels
- Beach Hotels in Lee
- Lgbt Welcoming Hotels in Lee
- Luxury Hotels in North Adams
- Pet Friendly Hotels in North Adams
- Cheap Hotels in Lenox
- Golf Hotels in The Berkshires
- Spa Hotels in Adams
- Visit Cheshire
- Visit The Berkshires
- Visit Great Barrington
- Visit West Stockbridge
- Visit Middlefield
- Visit Hawley
- Visit Williamstown
- Visit Tyringham
- Visit North Adams
- Visit Otis
- Charlemont Holidays
- Goose Pond Reservation
- Massachusetts Museum of Contemporary Art
- Otis Holidays
- G. William Pitt House and Collection
- Deerfield Academy
- Chicopee Holidays
- Ski Butternut
- North Adams Holidays
- National Shrine of the Divine Mercy
- Greenfield Community College
- Sterling and Francine Clark Art Institute
- Arthur A. Smith Covered Bridge
- Cheshire Holidays
- Williams College
- Norman Rockwell Museum
- Hadley Farm Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
