Cheap Flights to The Berkshires from $50
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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 $98 and $50 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* |
|---|---|---|---|
| RSW | Windsor Locks | August 11 to August 18 | $102 |
| JFK | Windsor Locks | June 11 to June 28 | $137 |
| RSW | Latham | August 21 to August 28 | $173 |
| JFK | Latham | June 25 to June 26 | $294 |
| MAN | Latham | June 25 to July 1 | $941 |
| MAN | Windsor Locks | June 12 to June 27 | $1,019 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Windsor Locks | June 6 to June 8 | $140 |
| RSW | Windsor Locks | June 6 to June 7 | $200 |
| RSW | Latham | June 8 to June 19 | $481 |
| JFK | Latham | June 7 to June 17 | $638 |
The Berkshires Flight Information
Traveling to | The Berkshires |
|---|---|
Lowest Price | $98 |
Number of Airlines Serving | |
Airlines Serving | Spirit Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing The Berkshires Accommodation Deals
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
Families like: Kids pool, playground, game room, skiing nearby
Reviewed on Jun 1, 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 For After Your Flight?
Special
$48
Economy Special
$50
Compact
$50
Midsize
$52
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!