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666 Travelers rated Pittsfield highly for Baseball and Sports

Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!
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Book a package and join the 188 others who’ve received 100% off their flights this year!

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Top Rated Hotels for your Pittsfield Vacation

Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
3.0 out of 5.0 1032 South Street, Pittsfield, MA
Free Cancellation
4.7/5 (12 reviews)

Friendly and efficient staff, very clean, large room,

Reviewed on Jun 7, 2019
Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and ...
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 out of 5.0 8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
4.2/5 (8 reviews)

Good, responsive maintenance staff. Property well maintained.

Reviewed on Aug 10, 2019
Situated in Pittsfield, this golf lodge is 1.1 mi (1.8 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater ...
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5.0 1350 W Housatonic St, Pittsfield, MA
Free Cancellation
4.1/5 (45 reviews)

It was ok. Average I guess. Old property but clean. Like the fact there was always someone at front desk

Reviewed on Sep 3, 2019
Situated near the airport, this hotel is 1.8 mi (2.9 km) from Hancock Shaker Village and 3 mi (4.9 km) from Bousquet Ski Area. Colonial Theater and Pittsfield ...

Tips for planning your Pittsfield vacation

Pittsfield flight + hotel dealFrom
Cheapest time to go to PittsfieldJanuary
Most expensive time to go to PittsfieldAugust
Pittsfield peak seasonJuly, August, June
Pittsfield low seasonDecember, January, November

Pittsfield Vacation Package Deals

The team here at Orbitz will assist you to bundle your flights and hotels to save money and time. Just pick a deal and start packing for that epic adventure to Pittsfield.

So, what are the benefits of bundling? Combine your airfares, hotels, experiences and rental cars with us and you could easily save up to $857*!

And remember — you'll be able to customize your trip by picking from 500 airlines and no less than 500,000 hotels across the world. You have the freedom to choose!

Secure a package deal that fits with you and your individual style. There are unlimited room types, flight options and unforgettable adventures only a few clicks away.

Join Orbitz Rewards

Bothersome paperwork, cards and forms — who wants that? We've created a simple program. Just keep booking with us and you'll get instant Orbucks!

Redeem your Orbitz Rewards points the next time you book. If you secure four nights in a full year, you'll become a gold member; 12 stays means platinum membership. Special perks at Orbitz Rewards VIP Hotels are available for all platinum and gold members.

Pittsfield Travel Guide

Where is Pittsfield?

Before you take off on your epic adventure to Pittsfield, it's probably a good idea to find out where it is first. (It could also save you some embarrassment when your friends ask exactly where you're going!)

You'll discover it approximately 110 miles west of Boston, the state capital of Massachusetts, and about 14 miles southwest of Adams.

This area of The Berkshires is home to nearly 45,000 people.

Places to Visit in Pittsfield

Arrowhead Museum is home to a comprehensive range of historical exhibits, allowing visitors to uncover the people and stories that shaped this area. Need some more options? Bousquet Ski Area is renowned as one of the top ski fields in the area, with a family-friendly environment where the little ones can also enjoy some fun on the slopes. But that's not all there is! Canoe Meadows Wildlife Sanctuary is perfect for a relaxing family excursion. You and the kids can explore the outdoors as well as learn how this unique area is being protected.

Car Rentals in Pittsfield

How about discovering the region your own way? Be the architect of your own epic adventure by checking out car rentals in Pittsfield with the help of Orbitz.

Enterprise can be found in the center of town at 526 East St. If your accommodation is nearby, this is place to go to.

Where to stay in Pittsfield – Hotel Accommodation

Ready to kick off your vacation? Book your room now! Orbitz has at least 21 hotels in Pittsfield.

Want us to help with your booking? We recommend the Hotel On North and Birchwood Inn.

Nearest Airports to Pittsfield

Start your Pittsfield getaway smoothly by learning a little about Bradley International Airport, the nearest terminal. Abbreviated as BDL, it sits 45 miles southeast of Pittsfield's downtown area. It's also the main entry point for most travelers.

Popular Places to Visit Near Pittsfield

Pittsfield has plenty of things to do, but if you're wanting to see more of the region, you're in luck! You have internationally famed tourist attractions close at hand! The Egg entices travelers from every nation. Delmar, only 30 miles from Pittsfield, is a convenient base when visiting this world-famous attraction.

No Cancellation Fees

You can be certain that whatever the reason for canceling or revising your booking, we won't penalize you with a fee.^ Why not call your airline and hotel to check if they do the same?

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2018 to December 31, 2018 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.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.