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Pittsfield Hotel + Air Packages

Hancock Shaker Village
Arrowhead
Suite
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 802 reviews and posted 658 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
My husband and I were in Pittsfield a couple of weeks ago to attend a concert at Tanglewood. The hotel is a perfect location for those who wish to enjoy the highlights of all...
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2. Find the right flight
Crowne Plaza Pittsfield
#2 Hotel in Pittsfield
Crowne Plaza Pittsfield
“Great Place!” 09/18/2014
We stayed two nights with our little baby, the room was very big so we were comfortable also with the portable crib on it, everything was very clean, incredible bed, the hotel...
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2. Find the right flight
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*
Oct
$192 round trip
Nov
$192 round trip
Dec
$192 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.