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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 1,012 reviews and posted 914 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
Classy, charming, elegant!! My wife and I both agree that this hotel is as nice as a Ritz Carlton and Four Seasons! We were out here about 11 months ago and stayed at The...
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BEST WESTERN PLUS Berkshire Hills Inn & Suites
#2 Hotel in Pittsfield
BEST WESTERN PLUS Berkshire Hills Inn & Suites
“Accomadation” 07/01/2015
As a father of 3, the hotel provided excellent accommodation for my kids to sleep. I reserved a double bed room and needed two cots for my kids and although I arrived around 10PM...
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Yankee Suites Extended Stay
#3 Hotel in Pittsfield
Yankee Suites Extended Stay
Comfortable apartments in a convenient location. Sunny and spacious. The kitchen works - save money and cook your own dinners. Full-sized fridge and oven as well as microwave...
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Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travelers in the past 72 hours*
Jul
$225 round trip
Aug
$225 round trip
Sep
$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.