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Pittsfield Vacation Packages

Hancock Shaker Village
Arrowhead
Bistecca marsala
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 885 reviews and posted 722 candid photos for Pittsfield hotels. Book your Pittsfield vacation today!
Or build your own Pittsfield vacation package
BEST WESTERN PLUS Berkshire Hills Inn & Suites
#1 Hotel in Pittsfield
BEST WESTERN PLUS Berkshire Hills Inn & Suites
very clean rooms and reasonable rate but caring staff makes the experiance. A hot Breakfast is always better than the usual advertised continental breakfast, a good way to start...
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Crowne Plaza Pittsfield
#2 Hotel in Pittsfield
Crowne Plaza Pittsfield
I stayed in the hotel for nine days straight and so I have a pretty good feel for the place. The rooms are clean and well appointed. The bathroom is a bit cramped but for me...
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The Inn At Lenox View
#3 Hotel in Pittsfield
The Inn At Lenox View
I escorted a bus to Tanglewood and we stayed at The Comfort Inn. Jay, the manager was most accomodating and we were all very pleased with our rooms. The linens were first class...
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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*
Jan
$177 round trip
Feb
$177 round trip
Mar
$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 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.