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Pittsfield Vacation Packages

Hancock Shaker Village
Arrowhead
Hilton Garden Inn Lenox/Pittsfield
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 966 reviews and posted 824 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
Great bargain...nice full breakfast included. Very clean rooms and the hotel staff was very good. Great team there from desk to breakfast to house keeping. Good base location...
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Yankee Suites Extended Stay
#2 Hotel in Pittsfield
Yankee Suites Extended Stay
“Essentials” 03/26/2015
Good value for price. Very clean somewhat dated rooms, but spacious. Staff very helpful. Nice to have Landry in basement. 22 minutes from Jiminy Peak. Across the street front...
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Crowne Plaza Pittsfield
#3 Hotel in Pittsfield
Crowne Plaza Pittsfield
Nice room. Good buffet breakfast. Only thing that seemed odd was that there was no exhaust fan in the bathroom. Mirror got all fogged-up during shower even with the door open...
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Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travelers in the past 72 hours*
Jun
$196 round trip
Jul
$219 round trip
Aug
$219 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.