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.
Book On TripAdvisor Bonus Book your hotel on TripAdvisor — then save 20% on things to do for your trip. Use code BOOKTOSAVE.

Pittsfield Vacation Packages

Hancock Shaker Village
Arrowhead
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 1,716 reviews and posted 1,420 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
I've stayed at many hotels throughout my 29 years but this hotel is the best of the best! No room is the same and I love that fact! Every room has its own distinct charm and...
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 hotel is in Pittsfield, just over the line from Lenox, and is set back from the main road, so you don't hear any traffic noise. Odd numbered rooms face the back - the view is...
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
“best western” 07/22/2016
Great place to stay in the area, especially as there are no two night minimums, easily accessible to Lenox MA and in a quiet location. There is not much to do around the hotel but...
1. Find your perfect hotel
2. Find the right flight
Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travelers in the past 72 hours*
Aug
$197 round trip
Sep
$197 round trip
Oct
$197 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.