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Pittsfield Vacation Packages

Hancock Shaker Village
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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 1,978 reviews and posted 1,736 candid photos for Pittsfield hotels. Book your Pittsfield vacation today!
Or build your own Pittsfield vacation package
Hotel on North
#1 Hotel in Pittsfield
Hotel on North
We have traveled to Pittsfield 2 times in the last 9 months and both time we stay at Hotel on North. They are friendly, the Hotel is amazing - so unique - love how the history of...
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Hilton Garden Inn Lenox Pittsfield
#2 Hotel in Pittsfield
Hilton Garden Inn Lenox Pittsfield
Friendly staff new rooms , reasonable prices, breakfast, bar pretty good restaurant. What else could you ask for In a getaway in the Berkshire. The room had a microwave, a fridge...
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BEST WESTERN PLUS Berkshire Hills Inn & Suites
#3 Hotel in Pittsfield
BEST WESTERN PLUS Berkshire Hills Inn & Suites
We visited this hotel for one night in mid October 2016. We were warmly welcomed by a young man who listened intently to our questions re things to do and how to get to certain...
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Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travelers in the past 72 hours*
Dec
$213 round trip
Jan
$213 round trip
Feb
$213 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.