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Pittsfield Hotel + Air Packages

Hancock Shaker Village
Arrowhead
Bridge
Build your own Pittsfield vacation package
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 755 reviews and posted 667 candid photos for Pittsfield hotels. Book your Pittsfield vacation today!
BEST WESTERN PLUS Berkshire Hills Inn & Suites
#1 Hotel in Pittsfield
BEST WESTERN PLUS Berkshire Hills Inn & Suites
“Nice Hotel!!” 07/31/2014
We stayed here during camp visiting day and enjoyed the hotel. Its nothing fancy, but was clean and convenient. I didn't like the fact that we were required to stay over 2...
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Crowne Plaza Pittsfield
#2 Hotel in Pittsfield
Crowne Plaza Pittsfield
I've visited the crowne plaza, the room was nice, the morning newspaper is brought to your room's front door every morning. The breakfast was nice and fresh, no vegetables...
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Comfort Inn Pittsfield
#3 Hotel in Pittsfield
Comfort Inn Pittsfield
Thank you, Comfort Inn for taking us in at the absolute last minute after our original booking had been given away without notice. The gave us a great deal, with two joining...
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2. Find the right flight
Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travelers in the past 72 hours*
Aug
$214 round trip
Sep
$214 round trip
Oct
$214 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.