Cheap Flight Deals to The Berkshires MA from CA $215
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How to find cheap flights to The Berkshires?
The cheapest prices found with in the last 7 days for return flights were CA $193 and CA $215 for one-way flights to The Berkshires for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| JFK | Windsor Locks | July 21 to July 29 | CA $193 |
| RSW | Latham | June 26 to July 3 | CA $298 |
Your guide to flights to The Berkshires, MA
JetBlue Airways, American Airlines fly to The Berkshires, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to The Berkshires MA currently costs between CA $193 and CA $576. Prices vary, but for the best fares, travel in August when prices are at their lowest.
Top tips for finding cheap flights to The Berkshires
The cheapest flight for a round trip to The Berkshires is currently CA $193. When you search for flights to The Berkshires, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to The Berkshires for nearby days. The cheapest month to travel to The Berkshires is September from our list of deals available.
But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.
How to cancel flights to The Berkshires
We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.
Why you should book your flight to The Berkshires with Travelocity
We have top deals on plane tickets even for last minute flights to The Berkshires, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to The Berkshires for less.
Find The Perfect Hotel For After Your Flight
Amazing Place to Stay After Flight to The Berkshires
Pleasant Valley Motel West Stockbridge
Reviewed on May 25, 2025
Wagon Wheel Inn
Reviewed on Oct. 13, 2024
Lantern House Motel
Reviewed on Nov. 22, 2021
The Weathervane Motel
Reviewed on Oct. 1, 2020
Luxury Hotels in The Berkshires
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Reviewed on Jul. 27, 2024
The Orchards Hotel
Reviewed on Mar. 9, 2020
Lantern House Motel
Reviewed on Nov. 22, 2021
Wagon Wheel Inn
Reviewed on Oct. 13, 2024
Family Friendly Hotels in The Berkshires
Vacation Village in the Berkshires
Reviewed on May 27, 2025
Hotel Downstreet, Ascend Hotel Collection
Reviewed on May 24, 2025
Stay Berkshires
Reviewed on Dec. 4, 2024
Williamstown Motel
Reviewed on May 28, 2025
Best The Berkshires Flight and Hotel Packages
The Berkshires flight + hotel packages - economy flights
Need a car after flight to The Berkshires?
Economy
Compact
Midsize
SUV
Flights To The Berkshires
The Berkshires has a legendary draw for travelers who like their vacations quaint and quiet. Nestled between Massachusetts's Taconic Mountains and the Hudson Highlands, it is the perfect place for people who want to escape the hectic pace of city life. It's a largely rural area with seemingly endless options for outdoor recreation, and plenty of small towns that offer a lot of unique and delicious options for dining. When you fly to The Berkshires, you'll notice the slower pace of life here right away—a pace that has a rejuvenating effect on the minds and bodies of all visitors.
Transportation from PSF
The Berkshires flights land at Pittsfield Municipal Airport (PSF) in Berkshire County. Considering that this is a largely rural area, there aren't many public transportation options. You can call for a taxi while you find your luggage, or you can get a car at one of several nearby rental agencies. Some local hotels offer shuttle service to and from the airport for their guests; you can contact hotels in The Berkshires to see which ones offer this option. After you get settled in at your hotel, you may want to visit a restaurant for some nourishment. Thankfully., there are plenty of excellent places to dine in Monterey and New Marlborough. You may choose an option that's near your hotel—that way, you can start your vacation with a relaxing, no-fuss meal.
Enjoy the Culture and Beauty of The Berkshires
When you choose The Berkshires as your next vacation destination, you'll have seemingly endless fun activities to consider. There are wonderful art museums in Stockbridge, North Adams, and Williamstown. If you like wandering through nature, you can visit any of the beautiful local parks and stunning preserves. By booking vacations in The Berkshires here at Travelocity, you can save up to $537, leaving you with plenty of money to enjoy any activity in The Berkshires that catches your attention. Make your travel plans today!