Pittsfield Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 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
Find the Best Pittsfield Vacation Packages
Pittsfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ₩215,395 per night from Jul 27 to Jul 28
₩215,395
₩274,883 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"The room in lobby were great. The big front porch was actually a nice thing to have, because the fire pit was closed (and the guy worked the front desk at night said he didn’t have a key to start it.) The bar was closed. The boutique was closed and there really wasn’t anywhere else you could go. ..."
Reviewed on Jun 26, 2026
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Fully refundable
The price is ₩262,446 per night from Jul 6 to Jul 7
₩262,446
₩293,157 total
Jul 6 - Jul 7
includes taxes & fees
9.4/10 Exceptional! (116 reviews)
"Best hotel breakfast I have had in a long time. The breakfast attendant kept items well stocked. She made sure that vacated tables were cleaned and ready for the next guests to enjoy their meal. The room was kept very clean. I really enjoyed the fresh pancakes that were made to order by a pancake ..."
Reviewed on Jun 26, 2026
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ₩382,158 per night from Jul 7 to Jul 8
₩382,158
₩426,866 total
Jul 7 - Jul 8
includes taxes & fees
9.6/10 Exceptional! (869 reviews)
"Always a great experience at Hotel on North! Great, comfortable room with amazing bathroom. Helpful and friendly staff. Safe parking in the rear secured lot."
Reviewed on Jun 24, 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 Pittsfield attractions
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
