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Pittsfield Holiday Packages

Hancock Shaker Village
Arrowhead
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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 2,274 reviews and posted 2,193 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
“Library Suite” 21/09/2017
Stayed in the library suite for our anniversary trip and we were completely blown away. What a beautiful, unique room. Absolutely gorgeous. Friendly staff too. If you ever find...
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Hilton Garden Inn Lenox Pittsfield
#2 Hotel in Pittsfield
Hilton Garden Inn Lenox Pittsfield
This was our second stay at the Hilton Garden Inn and once again, it exceeded our expectations. All of the staff were very friendly and went above and beyond to ensure our...
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Best Western Plus Berkshire Hills Inn & Suites
#3 Hotel in Pittsfield
Best Western Plus Berkshire Hills Inn & Suites
very good overnight stay in the middle of a road trip. clean room, comfortable bed not too soft or hard. friendly staff and great price. arrived late at night and left very early...
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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*
Oct
US$163 return
Nov
US$163 return
Dec
US$163 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.