Pittsfield Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿4,531 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Pittsfield

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is ฿2,497 per night from 3 Nov to 4 Nov
฿2,497
฿3,515 total
3 Nov - 4 Nov
includes taxes & fees
8.8/10 Excellent! (678 reviews)
"Great lodge with 1 bedroom suites and fully stocked kitchens"

Reviewed on 7 Oct 2025

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is ฿3,350 per night from 2 Nov to 3 Nov
฿3,350
฿3,742 total
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (893 reviews)
"Room was clean & comfortable. Thank you! Parking was kind of far."

Reviewed on 5 Oct 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is ฿3,307 per night from 2 Nov to 3 Nov
฿3,307
฿3,694 total
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Clean place. Good breakfast and friendly staff"

Reviewed on 2 Oct 2025

Best Western Plus Berkshire Hills Inn & Suites
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.