Cheap Flights to Berkshire County from $29 (2026/2027)

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How Much Does it Cost To Fly To Berkshire County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Apr 30 - Sat, May 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$62 Roundtrip, found 1 day ago
$62
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Orlando Intl. to Bradley Intl., returning Sat, May 2, priced at $62 found 1 day ago
Thu, May 7 - Thu, May 14
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$66 Roundtrip, found 7 hours ago
$66
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, May 7 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Thu, May 14, priced at $66 found 7 hours ago
Tue, Jun 2 - Tue, Jun 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Jun 2 from Orlando Intl. to Bradley Intl., returning Tue, Jun 9, priced at $102 found 2 days ago
Thu, Apr 30 - Mon, May 4
MCO
Orlando Intl.
ALB
Albany Intl.
$129 Roundtrip, found 2 days ago
$129
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Apr 30 from Orlando Intl. to Albany Intl., returning Mon, May 4, priced at $129 found 2 days ago
Fri, Mar 6 - Mon, Mar 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$136 Roundtrip, found 9 hours ago
$136
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Mar 6 from Tampa Intl. to Bradley Intl., returning Mon, Mar 9, priced at $136 found 9 hours ago
Mon, May 11 - Sat, May 16
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$139 Roundtrip, found 10 hours ago
$139
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, May 11 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sat, May 16, priced at $139 found 10 hours ago
Sat, May 30 - Sat, Jun 6
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, May 30 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sat, Jun 6, priced at $147 found 2 days ago
Wed, May 13 - Wed, May 27
MCO
Orlando Intl.
BDL
Bradley Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, May 13 from Orlando Intl. to Bradley Intl., returning Wed, May 27, priced at $147 found 2 days ago
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksMarch 20 to March 23$130
RSWLathamJune 6 to June 13$132
RSWWindsor LocksJune 6 to June 14$142
JFKLathamMarch 18 to March 31$286
MANLathamMarch 12 to March 25$1,018
MANWindsor LocksJune 6 to June 16$1,186
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWWindsor LocksFebruary 27 to March 2$253
JFKWindsor LocksFebruary 27 to March 2$282
JFKLathamMarch 1 to March 10$298
RSWLathamFebruary 28 to March 4$337
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Brooks Motel
2.0-star property

The Brooks Motel

Apr 8 - Apr 15

7 night stay

Fort Lauderdale (FLL) to Albany (ALB)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $668, price is now $506 per person
$506
per person
found 12 hours ago
The Wiltwyck
3.5-star property

The Wiltwyck

Apr 8 - Apr 15

7 night stay

Fort Lauderdale (FLL) to Albany (ALB)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $877, price is now $643 per person
$643
per person
found 12 hours ago
Don't see what you're looking for?
See all available trips from Fort Lauderdale to Berkshire County
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Travelers ❤️ These Berkshire County 🏨

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
8.6/10 Excellent! (2,241 reviews)
Nice staff

Reviewed on Feb 16, 2026

Opens in a new windowVacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead are located nearby.
9/10 Wonderful! (847 reviews)
Yes great stay

Reviewed on Feb 18, 2026

Opens in a new windowBerkshire Mountain Lodge
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Williams College Schow Science Library and Denison Park are located nearby.
9.6/10 Exceptional! (576 reviews)
Beautiful inn, wonderful staff.

Reviewed on Feb 16, 2026

Opens in a new windowThe Williams Inn
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The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Guido's Marketplace and Bousquet Ski Area are located nearby.
9/10 Wonderful! (1,008 reviews)
Beautiful room with a fireplace.

Reviewed on Feb 19, 2026

Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Berkshire County?
Based on prices found over the last seven days on Travelocity, a roundtrip flight to Berkshire County started at as little as $62. If you're flexible with your dates, it will be easy to snap up a great bargain. This price was available on Travelocity for flights to Berkshire County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Berkshire County?
There are 15 airline companies offering flights to Berkshire County. If you're planning a journey to Pittsfield, consider American Airlines. This highly rated carrier operates roughly 381 services every month to Berkshire County's major city.
What is the cheapest month to fly to Berkshire County?
Spend more money on epic adventures and less on your airfare by visiting Berkshire County in April. This is the most inexpensive month to travel to this place based on Travelocity's direct return flight demand between January and December last year. Look through our selection of flights and enjoy a change of scenery without breaking your budget.
How can I check my flight status to Berkshire County?
"Trips" can fill you in when it comes to information related to your flight to Berkshire County. Our customer portal allows you to organize everything in the same place, from checking your flight status to making updates to your itinerary. Click on Trips at the top right of the Travelocity homepage and then sign in or create an account. Or you can download the Travelocity app and access your travel details while you're out and about. Whether you have the family flying with you or you're a solitary wanderer, all your bookings are right there in your pocket.
How do I find the best deals on flights to Berkshire County?
Being flexible with your dates will help you walk away with an awesome deal. Travelocity makes it a piece of cake to find your ideal fare through the "Flexible dates" feature. First, search for your flight to Berkshire County, then compare prices for surrounding dates by clicking the "Flexible dates" dropdown box above. Booking earlier and avoiding peak periods are other things you can do. In the last seven days, the best price for a return flight to Berkshire County was $62. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Berkshire County with Travelocity?
Look for cheap flights to Berkshire County with Travelocity and begin planning your next break away. With round-the-clock customer service throughout every stage of the process and our Price Match Guarantee, we take the fuss out of finding cheap family flights, hotels, activities and more. Nab a fabulous deal today and prepare for an unforgettable adventure.
What are the most popular flight routes to Berkshire County?
Take a look at these leading flight routes to Berkshire County and start planning your next great adventure:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 1,131 flights a month.
  • Chicago, IL (ORD-O'Hare Intl.) to Bradley Intl. Airport (BDL) - 1,048 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 866 flights a month.

How much is a flight to Berkshire County on average?
Based on prices found on Travelocity over the last seven days, roundtrip flights to Berkshire County cost between $62 and $1,186. When you're ready to take off, Travelocity will help you find a fare that won't blow your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Berkshire County?
To get an idea of the average airborne time of a direct flight to Berkshire County, browse through these top routes:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 15 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 9 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 1 hour and 12 minutes

What can I expect on a flight to Berkshire County?
How long your flight takes and whether you're traveling with a low-cost or full-service airline will mostly determine this. If you're searching for long-haul flights to Berkshire County, drinks, meals and entertainment should come as standard. Want cheap flights for family vacations? Look into the deals from budget carriers. Normally, these airlines don't offer as many inclusions, so be prepared to pay for your drinks and meals.

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