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New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

Pittsfield Holiday Packages

Hancock Shaker Village
Arrowhead
Suite
Pittsfield Holiday Packages
Want to book a holiday to Pittsfield? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Pittsfield holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Pittsfield on TripAdvisor by comparing Pittsfield hotel and flight prices. Travellers like you have written 1,974 reviews and posted 1,694 candid photos for Pittsfield hotels. Book your Pittsfield holiday today!
Or build your own Pittsfield holiday package
Hotel on North
#1 Hotel in Pittsfield
Hotel on North
This was by far one of the best hotel experiences I have ever had and I have traveled a ton both domestically and abroad. Exceptional in every way, the Hotel on North is a lovely...
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Hilton Garden Inn Lenox Pittsfield
#2 Hotel in Pittsfield
Hilton Garden Inn Lenox Pittsfield
This hotel was a pleasure from check in to check out. The bed was comfortable .The shower and amount of towels was great.The staff were beyond friendly and helpful. The...
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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 travellers in the past 72 hours*
Dec
US$213 return
Jan
US$213 return
Feb
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.