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Pittsfield Holiday Packages

Hancock Shaker Village
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Hotel Exterior
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 2,396 reviews and posted 2,281 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
The pictures online held great promise and I am happy to report that the hotel actually exceeded my expectations. I was delighted with the fresh, unfussy - yet carefully curated...
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Hilton Garden Inn Lenox Pittsfield
#2 Hotel in Pittsfield
Hilton Garden Inn Lenox Pittsfield
Love being a Hilton Honors member..Great service, excellent accommodations...love the friendliness and cleanliness! never have had a bad stay in a Hilton Garden Inn, but this one...
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Best Western Plus Berkshire Hills Inn & Suites
#3 Hotel in Pittsfield
Best Western Plus Berkshire Hills Inn & Suites
I travel a lot and always stay at the Best Western. My husband and I loved this hotel, the breakfast was amazing and the room was super clean! The staff was very friendly and...
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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$170 round trip
Jan
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Feb
find price 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.