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Pittsfield Holiday Packages

Hancock Shaker Village
Arrowhead
Putting sesame seeds on the bagels.
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 2,005 reviews and posted 2,007 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
Full disclosure, I live right in town and know the owners - but my best friend was getting married and used HoN as the headquarters for rehearsal dinner and prepping. I thought...
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Hilton Garden Inn Lenox Pittsfield
#2 Hotel in Pittsfield
Hilton Garden Inn Lenox Pittsfield
Comfortable room, very clean, fairly new. 2 years old. I think the only thing missing is a magnifying mirror in the bath. They actually have a cocktail bar and hot breakfast...
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Best Western Plus Berkshire Hills Inn & Suites
#3 Hotel in Pittsfield
Best Western Plus Berkshire Hills Inn & Suites
Stayed just one night on our way to Maine but would return. Front desk staff friendly and helped find a good restaurant close by. Room was quiet and clean. Nice breakfast to...
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Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travellers in the past 72 hours*
Jun
US$213 round trip
Jul
US$213 round trip
Aug
US$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 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.