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 ฿4,602 per night from 19 Jul to 20 Jul
฿4,602
฿5,873 total
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (989 reviews)
"Location was perfect"
Reviewed on 19 Jun 2026
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ฿8,164 per night from 22 Jun to 23 Jun
฿8,164
฿9,120 total
22 Jun - 23 Jun
includes taxes & fees
9.6/10 Exceptional! (866 reviews)
"The whole experience was great. Staff excellent."
Reviewed on 16 Jun 2026
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Fully refundable
The price is ฿4,590 per night from 29 Jun to 30 Jun
฿4,590
฿5,128 total
29 Jun - 30 Jun
includes taxes & fees
9.4/10 Exceptional! (108 reviews)
"The room and common areas were immaculate! The staff couldn’t have been more welcoming!"
Reviewed on 18 Jun 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.
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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.
