
Pittsfield Packages (Flight + Hotel)
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Top hotels in Pittsfield

Berkshire Mountain Lodge
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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

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