Cheap Flight Deals to The Berkshires MA from CA $282
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
How to find cheap flights to The Berkshires?
The cheapest prices found with in the last 7 days for return flights were CA $180 and CA $282 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 | January 8 to January 11 | CA $180 |
| RSW | Windsor Locks | December 31 to January 5 | CA $374 |
| JFK | Latham | January 6 to January 13 | CA $433 |
Your guide to flights to The Berkshires, MA
Delta, American Airlines, WestJet 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 $180 and CA $561. Prices vary, but for the best fares, travel in April 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 $180. 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 January 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
Priced very reasonably and the room was clean and comfy!
Reviewed on Dec 4, 2025
Wagon Wheel Inn
Good overall.
Reviewed on Oct 26, 2025
Lantern House Motel
The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ...
Reviewed on Nov 22, 2021
The Weathervane Motel
Booked a king bed but when I got there they told me no cable in that room. They gave me a room with a double bed that were on top of being small were very uncomfortable plus so much dust in air conditioner my allergies were affected plus it stunk couldn’t stay had to repack and go drive around and ...
Reviewed on Oct 1, 2020
Luxury Hotels in The Berkshires
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!
Reviewed on Oct 27, 2025
The Orchards Hotel
A little dated. Restaurant shut down for renovations, disappointing
Reviewed on Mar 9, 2020
Lantern House Motel
The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ...
Reviewed on Nov 22, 2021
Wagon Wheel Inn
Good overall.
Reviewed on Oct 26, 2025
Family Friendly Hotels in The Berkshires
Vacation Village in the Berkshires
Clean spacious toom
Reviewed on Dec 6, 2025
Hotel Downstreet, an Ascend Collection Hotel
I don’t have a single complaint about this hotel! Everything was perfect! Staff was great, parking was easy, everything was clean! My family and I will definitely be staying here again in the future!
Reviewed on Dec 5, 2025
Stay Berkshires
Nice option to stay near MASS MOCA.
Reviewed on Dec 4, 2024
Williamstown Motel
Room was very clean. Spoke to staff on the way in who was very courteous about our late arrival. Continental breakfast was accommodative. Free visitor materials were helpful. 😊
Reviewed on Nov 23, 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
Frequently asked questions
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!
Near The Berkshires
Airports in The Berkshires
Most Popular
- All Inclusive Resorts & Hotels in Oahu
- All Inclusive Resorts & Hotels in Kauai
- Hotels near Wrentham Village Premium Outlets
- Hotels near Gillette Stadium
- Pet Friendly Hotels in Cape Cod
- All Inclusive Resorts & Hotels in Maui
- Beach Resorts & Hotels in Cape Cod
- Golf Resorts & Hotels in Upstate New York
- Hotels in Kauai
- All Inclusive Resorts & Hotels in Cape Cod
- Hotels in Maui
- Waterpark Hotels and Resorts in Upstate New York
- Hotels in Downtown Boston
- Hotels in Salem
- Hotels in Oahu
- Hotels in Cape Cod