Pittsfield Packages (Flight + Hotel)

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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 ฿2,654 per night from 26 Apr to 27 Apr
฿2,654
฿3,685 total
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (914 reviews)
Great place and pool

Reviewed on 24 Apr 2026

Berkshire Mountain Lodge
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ฿4,841 per night from 27 Apr to 28 Apr
฿4,841
฿5,407 total
27 Apr - 28 Apr
includes taxes & fees
9.6/10 Exceptional! (845 reviews)
Awesome boutique rooms!

Reviewed on 21 Apr 2026

Hotel On North
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 ฿3,704 per night from 3 May to 4 May
฿3,704
฿4,137 total
3 May - 4 May
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Staff was nice. Room was clean. Parking lot was under construction. Had to park offsite. Wasn't a total inconvenience. One elevator was broken and the wait time was long each time we were trying to use.

Reviewed on 19 Apr 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.