Cheap Flights to The Berkshires from $34
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How Much Does it Cost To Fly To The Berkshires?
The cheapest prices found with in the last 7 days for return flights were $89 and $34 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 | December 2 to December 16 | $89 |
| RSW | Latham | December 6 to December 9 | $133 |
| RSW | Windsor Locks | January 9 to January 18 | $137 |
| JFK | Latham | December 10 to December 17 | $279 |
| MAN | Windsor Locks | January 23 to January 26 | $813 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| RSW | Latham | November 9 to November 11 | $178 |
| RSW | Windsor Locks | November 9 to November 17 | $200 |
| JFK | Windsor Locks | November 7 to November 9 | $271 |
| JFK | Latham | November 8 to November 10 | $469 |
The Berkshires Flight Information
Traveling to | The Berkshires |
|---|---|
Lowest Price | $89 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, Breeze Airways |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
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
Families like: Kids pool, playground, game room, skiing nearby
Good location; reasonable price; very clean and quiet - would definitely return
Reviewed on Oct 27, 2025
Hotel Downstreet, an Ascend Collection Hotel
Kind staff!
Reviewed on Oct 28, 2025
Stay Berkshires
Nice option to stay near MASS MOCA.
Reviewed on Dec 4, 2024
Williamstown Motel
Great location with easy parking
Reviewed on Oct 26, 2025
Best The Berkshires Flight and Hotel Packages
The Berkshires flight + hotel packages - economy flights
Need a Car For After Your Flight?
Economy
Compact
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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!
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