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Pittsfield Holiday Packages

Hancock Shaker Village
Arrowhead
Liked the sweet potato fries
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 2,116 reviews and posted 2,087 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 hotel is a real find! Perfect for a visit to the Berkshire! Loved our room, service, and food at adjacent restaurants. Parking available behind the hotel in a secure lot...
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Hilton Garden Inn Lenox Pittsfield
#2 Hotel in Pittsfield
Hilton Garden Inn Lenox Pittsfield
I stayed here for 5 nights with a group of Road Scholars visiting Tanglewood. The hotel is about 2 years old and is bright and clean. It even has solar panels! The bedroom was...
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Best Western Plus Berkshire Hills Inn & Suites
#3 Hotel in Pittsfield
Best Western Plus Berkshire Hills Inn & Suites
“Will be back” 25/07/2017
This wasn't our first and it won't be our last. We stay here every year when we drop off and pick up my daughter from at Camp Danbee. Staff is awesome. Rooms are super clean. Beds...
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Cheap Flights to Pittsfield
All Washington to Albany (WAS-ALB) fares found by travellers in the past 72 hours*
Aug
USD 213 return
Sep
USD 213 return
Oct
USD 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.