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Cheap Vacations in Pittsfield

Choose one or more items to build your trip:

3-night Pittsfield vacations

CrestHill Suites SUNY University Albany
Cocca's Inn & Suites Wolf Rd, Albany Airport
Red Roof Inn Clifton Park
Pine Bush Suites Albany University
SureStay Plus Hotel by Best Western Albany Airport
Super 8 by Wyndham Kingston
Courtyard by Marriott Albany Clifton Park
Red Roof Inn Albany Airport
Super 8 by Wyndham Latham/Albany Troy Area
Marriott Albany

Pittsfield Vacation Deal FAQ's

Where to find Pittsfield package deals?

On CheapTickets, you can find package deals in Pittsfield as low as $271!

When is peak season in Pittsfield?

July, August, June are very popular times to visit Pittsfield.

When is the best time to visit Pittsfield?

If you're looking for cheap vacations to Pittsfield, January is the best time to visit Pittsfield.

When is the worst time time to visit Pittsfield?

Prices for Pittsfield vacations can peak during August.

When is low season in Pittsfield?

We have found December, January, November to be the least-crowded time of the year to visit Pittsfield.

Where is Pittsfield?

Do you appreciate exploring the globe for less? Are you a connoisseur of stretching your dollar? It's time you took your cheaptastic self to Pittsfield!

It sits 16 miles to the south-west of Adams, and 317 miles to the north-east of Washington, the nation's capital.

Roughly 44,700 people reside in this part of Berkshire County, so there are plenty of opportunities to make new friends.

Cheap Things to do in Pittsfield

Don't stress about admission prices, booking fees and expensive activities! With our suggestions for free things to do in or near Pittsfield, you'll be sitting pretty with the best thrifty travel hacks:

  • The Crane Museum of Papermaking doesn't charge an entry fee! If you're close by, check it out and expand your mind — you just don't know what you could find.
  • Charge your camera and devote some time to taking pics of the Berkshire Athenaeum and Guido's Marketplace.
  • Whether it's winter or autumn, you're bound to enjoy the natural surrounds at Canoe Meadows Wildlife Sanctuary. With no pricey entrance fees, it's a fantastic place to swing by in every season.

Cheap Pittsfield Vacation Package Deals

Don't panic about sifting through the web for the thriftiest prices on hotels, travel and vacation activities. CheapTickets has sorted it out for you, and we definitely haven't made any trade-offs on quality and comfort.

To travel on a small budget is to forfeit all sorts of options, right? Wrong! With 500 airline partners and over 500,000 properties all over the world, you're swimming in choice. And the best part is you can save up to $290^ when you simply combine your bookings on flights and hotels.

You'll always get the cheapest prices — it's our guarantee. We'll reimburse you the difference if you find your vacation package for a cheaper price within 48 hours of making your booking. That's our Price Guarantee.

Get CheapCash

Book those flights, earn some CheapCash and use it on your next qualifying CheapTickets hotel booking. Our rewards program doesn't get much simpler than that. So, what are you waiting around for?

Savings on eligible bookings — check! Bonus offers and perks as far as the eye can see — check! All that's left is for you to log in or sign up for free, join CheapCash and experience the rewards!

Cheap Car Rentals in Pittsfield

We know you love cheap, so why not get yourself a rental car in Pittsfield? It's not only a brilliant way of getting around, it'll save you money too.

Consider renting a car from Hertz at PITTSFIELD HLE 811 DALTON AVENUE. They are right in the city center. You can also check out Enterprise at 526 EAST ST.

Cheap Hotels in Pittsfield

If you're a savvy traveler, you'll know the advantage of booking somewhere to stay in advance. You'll find 25 hotels in Pittsfield — let CheapTickets help you lock in the hottest deal!

Spend your nights in comfort at the Yankee Suites Extended Stay and the Berkshire Inn. Whichever option you decide on, it will make a great base for your island escape!

Flight deals to Pittsfield

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, May 26
RSW
Fort Myers
ALB
Albany
$117
Bargain Flight
Wed, May 26
RSW
Fort Myers
ALB
Albany
$119
United
Wed, May 26
RSW
Fort Myers
ALB
Albany
$119
Delta
Wed, May 19 - Tue, May 25
RSW
Fort Myers
ALB
Albany
$237
United
Wed, May 5 - Tue, May 18
RSW
Fort Myers
ALB
Albany
$237
Delta
Thu, May 20 - Tue, May 25
RSW
Fort Myers
ALB
Albany
$257
American Airlines

Top rated hotels for your Pittsfield vacation

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.