We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Want the lowest hotel prices? You're in the right place. We check 200+ sites for you.

Pittsfield Holiday Packages

Hancock Shaker Village
Arrowhead
Breakfast Bar
Pittsfield Holiday Packages
Want to book a holiday to Pittsfield? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Pittsfield holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Pittsfield on TripAdvisor by comparing Pittsfield hotel and flight prices. Travellers like you have written 1,919 reviews and posted 1,809 candid photos for Pittsfield hotels. Book your Pittsfield holiday today!
Or build your own Pittsfield holiday package
Hotel on North
#1 Hotel in Pittsfield
Hotel on North
This is our second winter break visit to the Berkshires and to this hotel. Hotel on North is a very smart investment in downtown Pittsfield. The owners have presented a stunning...
1. Find your perfect hotel
2. Find the right flight
Hilton Garden Inn Lenox Pittsfield
#2 Hotel in Pittsfield
Hilton Garden Inn Lenox Pittsfield
This is a great hotel. It is super clean and very centrally located. The entire staff is very friendly and helpful. The food at the hotel is quite good. I highly recommend...
1. Find your perfect hotel
2. Find the right flight
BEST WESTERN PLUS Berkshire Hills Inn & Suites
#3 Hotel in Pittsfield
BEST WESTERN PLUS Berkshire Hills Inn & Suites
Visited with family for skiing; Bousquet a small/local mountain was affordable and very close by. We also went to the outlets and tried some local cuisine. We had a suite with...
1. Find your perfect hotel
2. Find the right flight
Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travellers in the past 72 hours*
Mar
US$213 return
Apr
US$213 return
May
US$213 return
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travellers 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.