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Pittsfield Vacation Packages

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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 905 reviews and posted 759 candid photos for Pittsfield hotels. Book your Pittsfield vacation today!
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BEST WESTERN PLUS Berkshire Hills Inn & Suites
#1 Hotel in Pittsfield
BEST WESTERN PLUS Berkshire Hills Inn & Suites
we were meeting my sister and her husband in Pittsfield. We needed a place we could spend the night but have space to sit around and talk. The 2 room suite worked great. The...
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Yankee Suites Extended Stay
#2 Hotel in Pittsfield
Yankee Suites Extended Stay
We stayed only one night in January but everything was in order. Very clean, comfortable, and spacious. We didn't do any cooking but there was a nice size kitchen plus glasses...
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Crowne Plaza Pittsfield
#3 Hotel in Pittsfield
Crowne Plaza Pittsfield
I can't compliment the staff of this hotel enough! The hotel was clean and food in the restaurant/Bar was great! We stayed for two nights with a group for a hockey tournament...
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2. Find the right flight
Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travelers in the past 72 hours*
Feb
$196 round trip
Mar
$196 round trip
Apr
$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.