Cheap Flights to The Berkshires from $49
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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 $88 and $49 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 | Latham | May 16 to May 23 | $125 |
| JFK | Windsor Locks | May 11 to May 14 | $177 |
| RSW | Windsor Locks | May 13 to May 17 | $179 |
| JFK | Latham | June 4 to June 10 | $339 |
| MAN | Windsor Locks | April 29 to May 3 | $964 |
| MAN | Latham | April 27 to May 11 | $1,162 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| RSW | Latham | April 18 to April 25 | $294 |
| JFK | Latham | April 18 to April 22 | $446 |
| JFK | Windsor Locks | April 18 to April 28 | $448 |
| RSW | Windsor Locks | April 19 to April 19 | $558 |
The Berkshires Flight Information
Traveling to | The Berkshires |
|---|---|
Lowest Price | $88 |
Number of Airlines Serving | |
Airlines Serving | Frontier 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
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
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
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
Families like: Kids pool, playground, game room, skiing nearby
Very nice
Reviewed on Apr 12, 2026
Hotel Downstreet, an Ascend Collection Hotel
Nice staff comfy bed nice views
Reviewed on Apr 8, 2026
Williamstown Motel
Cozy Corner Motel
Families like: Lazy river, playground, skiing nearby, free breakfast for the whole family
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 For After Your Flight?
Special
$30
Midsize Special
$44
Economy
$46
Compact
$46
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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