Cheap Flight Deals to The Berkshires MA from CA $154
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 $248 and CA $154 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 | May 9 to May 10 | CA $248 |
Your guide to flights to The Berkshires, MA
Breeze Airways, Delta, WestJet, 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 $248 and CA $573. Prices vary, but for the best fares, travel in May 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 $248. 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 May 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
I used heat and it worked
Reviewed on Apr 3, 2026
Wagon Wheel Inn
We've been in worse, but not by much. It kept the wind out of our hair and the shower had plenty of hot water. That's about it
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
The Orchards Hotel
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
We've been in worse, but not by much. It kept the wind out of our hair and the shower had plenty of hot water. That's about it
Reviewed on Oct 26, 2025
Family Friendly Hotels in The Berkshires
Vacation Village in the Berkshires
While this is a good value for the money for a one bedroom with separate kitchenette and living area, this is basically 2nd or 3rd rate for a timeshare unit. Couch is uncomfortable to sit on and bed isn't the best. Didn't provide some very basics, such as dish soap to wash dishes and pans which are ...
Reviewed on Apr 18, 2026
Hotel Downstreet, an Ascend Collection Hotel
Staff is always welcoming & accommodating. Had and issue with a noisy dog in the room below our room; when I notified the front desk, they tried to deal with it; when that failed, they were quite willing to move us to a different room.
Reviewed on Apr 21, 2026
Williamstown Motel
The hotel booking has breakfast included but the owner couldn't provide due to her own condition and even refuse to provide partial refund. The owner promised to provide additional blankets but didn't. Further no instruction in the room to get the wifi connection. Very poor management!
Reviewed on Apr 20, 2026
Cozy Corner Motel
Cute, old hotel. Very clean! Room smelled a little musty, otherwise everything was excellent. Staff was very nice.
Reviewed on Apr 13, 2026
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!
Explore More Ways to Travel with Travelocity
- 4 Star Hotels in The Berkshires
- Agawam Hotels
- Cabins in Amherst
- Amherst Hotels
- Hotels near Berkshire Athenaeum
- Blandford Hotels
- Buckland Hotels
- Cabins in Chicopee
- Chicopee Hotels
- Conway Hotels
- Dalton Hotels
- Drury Hotels
- East Longmeadow Hotels
- Hotels near Eastern States Exposition
- Easthampton Hotels
- Florence Hotels
- Granville Hotels
- Golf Resorts & in Great Barrington
- Great Barrington Hotels
- Vacation Homes in Great Barrington
- Hadley Hotels
- Cabins in Holyoke
- Historic Hotels in Holyoke
- Hotels with Hot Tubs in Holyoke
- Pet Friendly Hotels in Holyoke
- Holyoke Hotels
- Hotels near Holyoke Mall
- Cottages in Lee
- Cottages in Lenox
- Lenox Hotels
- Longmeadow Hotels
- Monterey Hotels
- Hotels near Mount Greylock
- Hotels near National Shrine of the Divine Mercy
- New Marlborough Hotels
- Northampton Hotels
- Richmond Hotels
- Hotels near Six Flags New England
- South Egremont Hotels
- South Hadley Hotels
- Southampton Hotels
- Cottages in Southwick
- Pet Friendly Hotels in Springfield
- Springfield Hotels
- Stockbridge Hotels
- Hotels near Tanglewood Music Center
- Apartments in The Berkshires
- B&B in The Berkshires
- Cabins in The Berkshires
- Condos in The Berkshires
- Cottages in The Berkshires
- Luxury Hotels in The Berkshires
- Romantic Getaways & Hotels in The Berkshires
- Ski Resorts and in The Berkshires
- Spa Resorts & in The Berkshires
- Lodges in The Berkshires
- West Springfield Hotels
- Cabins in Western Massachusetts
- Westfield Hotels
- Williamstown Hotels
- Ace New Zealand Rental Cars in North Adams
- Avis Rental Cars in Otis
- Car rental Adams
- Car rental Lee
- Discount Car Rentals Rental Cars in Holyoke
- Drive on Holidays Rental Cars in Southwick
- First Car Rental Rental Cars in Becket
- First Car Rental Rental Cars in Southwick
- Global Rent a Car Rental Cars in North Adams
- Island Car Rentals Rental Cars in Adams
- Island Car Rentals Rental Cars in Easthampton
- Island Car Rentals Rental Cars in Otis
- Island Car Rentals Rental Cars in Southwick
- Island Car Rentals Rental Cars in Williamstown
- Maggiore Rental Cars in North Adams
- Mex Rent A Car Rental Cars in Northampton
- Ok Mobility Rental Cars in Northampton
- Right-Cars Rental Cars in East Longmeadow
- Right-Cars Rental Cars in Hatfield
- Right-Cars Rental Cars in Western Massachusetts
- Sicily By Car Rental Cars in Northampton
- Surprice Car Rentals Rental Cars in East Longmeadow
- Top Rent a Car Rental Cars in East Longmeadow