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Pittsfield Hotel + Air Packages

Hancock Shaker Village
Arrowhead
Lobby Lounge
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 780 reviews and posted 638 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 stay” 08/31/2014
Overall a nice overnight stay. We were a little surprised how far away the hotel was from Tanglewood in Lenox, MA. The hotel is very clean and ameneties are very good. The...
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Comfort Inn Pittsfield
#2 Hotel in Pittsfield
Comfort Inn Pittsfield
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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Crowne Plaza Pittsfield
#3 Hotel in Pittsfield
Crowne Plaza Pittsfield
This hotel was clean, comfortable and had a very helpful, friendly staff. Nice pool for the kids, although it had way too much chlorine....big minus really. Otherwise, we...
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Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travelers in the past 72 hours*
Sep
$186 round trip
Oct
$209 round trip
Nov
find price 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.