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Pittsfield Holiday Packages

Hancock Shaker Village
Arrowhead
Liked the sweet potato fries
Pittsfield Holiday Packages
Want to book a vacation to Pittsfield? Whether you are 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 2,106 reviews and posted 2,081 candid photos for Pittsfield hotels. Book your Pittsfield vacation today!
Or build your own Pittsfield holiday package
Hotel on North
#1 Hotel in Pittsfield
Hotel on North
Do you think we like this place? Wrong! We love it! We always take an Extended Stay Room and enjoy the kitchenette and washer/dryer conveniences. With all of the choices for...
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Hilton Garden Inn Lenox Pittsfield
#2 Hotel in Pittsfield
Hilton Garden Inn Lenox Pittsfield
“Wedding Trip” 24/07/2017
Excellent experience at a wonderful hotel. Perfect location. Hotel offered everything we needed from a very comfortable room to an awesome fitness center to a tasty breakfast...
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Best Western Plus Berkshire Hills Inn & Suites
#3 Hotel in Pittsfield
Best Western Plus Berkshire Hills Inn & Suites
Upon check in we were greeted by two great employees. I asked about storing our two bikes somewhere inside rather than in my room or on my car. They found a locked spot inside the...
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2. Find the right flight
Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travellers in the past 72 hours*
Aug
US$213 return
Sep
US$213 return
Oct
US$213 return
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travellers 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.