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Pittsfield Vacation Packages

Hancock Shaker Village
Arrowhead
Elevator Lobby
Pittsfield Vacation Packages
Want to book a vacation to Pittsfield? Whether you're 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 1,080 reviews and posted 1,023 candid photos for Pittsfield hotels. Book your Pittsfield vacation today!
Or build your own Pittsfield vacation package
Hotel on North
#1 Hotel in Pittsfield
Hotel on North
Never been to a restaurant like this before An odd and limited menu, ranging from calamari or octopus to macaroni and cheese w/a hotdog. So had a hamburger for dinner, and it was...
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BEST WESTERN PLUS Berkshire Hills Inn & Suites
#2 Hotel in Pittsfield
BEST WESTERN PLUS Berkshire Hills Inn & Suites
“Very pleased” 07/31/2015
We had a lovely overnight stay here. Good location just outside of the center of the city which we preferred. Staff was friendly and helpful. Two-room suite with sitting room...
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Yankee Suites Extended Stay
#3 Hotel in Pittsfield
Yankee Suites Extended Stay
Comfortable apartments in a convenient location. Sunny and spacious. The kitchen works - save money and cook your own dinners. Full-sized fridge and oven as well as microwave...
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Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travelers in the past 72 hours*
Aug
find price round trip
Sep
$202 round trip
Oct
$210 round trip
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers 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.