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Pittsfield Vacation Packages

Hancock Shaker Village
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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 1,884 reviews and posted 1,730 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
“Enjoyed it” 01/17/2017
Change of pace from the cookie-cutter chains. The hotel is in great shape and very nice. Our room was decorated nicely with simple paint colors and a painted brick wall towards...
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Hilton Garden Inn Lenox Pittsfield
#2 Hotel in Pittsfield
Hilton Garden Inn Lenox Pittsfield
This hotel is great for families and very close to Jiminy Peak Ski Mountain. My family loved the hotel, restaurant, pool and hot tub! Nice job all around Hilton Garden Inn, we...
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BEST WESTERN PLUS Berkshire Hills Inn & Suites
#3 Hotel in Pittsfield
BEST WESTERN PLUS Berkshire Hills Inn & Suites
clean , well put together and staff is friendly. lots of bonuses like the good enough gym and also the breakfast, the food could be better but hey its there so i wont be too...
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Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travelers in the past 72 hours*
Feb
$213 round trip
Mar
$213 round trip
Apr
$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.