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Pittsfield Vacation Packages

Hancock Shaker Village
Arrowhead
2 Queen Beds w Pull-out couch
Pittsfield Vacation Packages
Want to book a vacation to Pittsfield? Whether you're off for a romantic vacation, family trip, or an all-inclusive holiday, Pittsfield vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Pittsfield on TripAdvisor by comparing Pittsfield hotel and flight prices. Travelers like you have written 867 reviews and posted 703 candid photos for Pittsfield hotels. Book your Pittsfield vacation today!
Or build your own Pittsfield vacation package
BEST WESTERN PLUS Berkshire Hills Inn & Suites
#1 Hotel in Pittsfield
BEST WESTERN PLUS Berkshire Hills Inn & Suites
would highly recommend this hotel, clean rooms, ultra comfy bed, super friendly staff. better than other hotels we had stayed at. we make this trip several times a year and our...
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Crowne Plaza Pittsfield
#2 Hotel in Pittsfield
Crowne Plaza Pittsfield
Overall really enjoyed the stay here. We stayed as a part of a College Soccer Team and the staff was so accommodating. They were able to put together a conference room and dinner...
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Berkshire Inn
#3 Hotel in Pittsfield
Berkshire Inn
The Berkshire Inn offers comfort and cleanliness. The king size bed was luxury with plenty of plump pillows. The front window treatment completely blocked out any light...
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Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travelers in the past 72 hours*
Dec
$190 round trip
Jan
$196 round trip
Feb
$216 round trip
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.