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Pittsfield Vacation Packages

Hancock Shaker Village
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It's a basement bar
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 919 reviews and posted 772 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
Needed a hotel room in a pinch in Pittsfield, MA. Chose The Best Western and couldn't have been happier. The free breakfast was simple but hit the spot and the 24 hour tea/coffee...
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Yankee Suites Extended Stay
#2 Hotel in Pittsfield
Yankee Suites Extended Stay
Excellent place, well maintained, very clean and spacious, well equipped kitchen, very dog friendly, management very friendly and accommodating, good location, close to ski areas...
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Crowne Plaza Pittsfield
#3 Hotel in Pittsfield
Crowne Plaza Pittsfield
Can't speak enough about the truly great friendly service shown by all staff. The bar, restaurant, house keeping, maintenance and especially the front desk, specifically Jessica...
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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*
Mar
$190 round trip
Apr
$191 round trip
May
$191 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.