Cheap Flights to Berkshire County from $73 (2026/2027)

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Lenox

Flights
Lenox

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.

Tue, Jun 9 - Wed, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$135 Roundtrip, found 1 day ago
$135
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jun 9 from Orlando Intl. to Bradley Intl., returning Wed, Jun 10, priced at $135 found 1 day ago
Sat, Jun 6 - Wed, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 6 hours ago
$137
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Orlando Intl. to Bradley Intl., returning Wed, Jun 10, priced at $137 found 6 hours ago
Thu, Sep 10 - Wed, Sep 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$182 Roundtrip, found 23 hours ago
$182
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Wed, Sep 16, priced at $182 found 23 hours ago
Mon, Aug 31 - Thu, Sep 3
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$187 Roundtrip, found 3 days ago
$187
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Aug 31 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Thu, Sep 3, priced at $187 found 3 days ago
Thu, Sep 10 - Sun, Sep 13
MCO
Orlando Intl.
ALB
Albany Intl.
$192 Roundtrip, found 21 hours ago
$192
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Albany Intl., returning Sun, Sep 13, priced at $192 found 21 hours ago
Sat, Jun 6 - Wed, Jun 10
MCO
Orlando Intl.
ALB
Albany Intl.
$212 Roundtrip, found 4 hours ago
$212
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Jun 6 from Orlando Intl. to Albany Intl., returning Wed, Jun 10, priced at $212 found 4 hours ago
Fri, Aug 14 - Tue, Aug 18
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Aug 14 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, Aug 18, priced at $217 found 4 days ago
Wed, Jul 1 - Sat, Jul 11
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$222 Roundtrip, found 16 hours ago
$222
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Wed, Jul 1 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sat, Jul 11, priced at $222 found 16 hours ago
OriginDestinationTravel DatesFlights From*
RSWLathamSeptember 2 to September 9$112
RSWWindsor LocksAugust 20 to August 27$152
JFKWindsor LocksJune 5 to June 7$192
JFKLathamJune 15 to June 22$361
MANWindsor LocksJune 25 to June 28$813
MANLathamJuly 12 to July 21$1,195
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWLathamMay 30 to June 3$169
JFKWindsor LocksMay 31 to June 3$202
RSWWindsor LocksMay 29 to May 31$204
JFKLathamMay 30 to June 3$391
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Cornell Inn, Lenox & The Berkshires
3.5-star property

The Cornell Inn, Lenox & The Berkshires

Jun 11 - Jun 14

3 night stay

Atlanta (ATL) to Albany (ALB)

Delta • Roundtrip • Coach
Price was $1,217, price is now $942 per person
$942
per person
found 17 hours ago
Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay
3.0-star property

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

Jun 25 - Jun 29

4 night stay

Fort Myers (RSW) to Albany (ALB)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $7,687, price is now $5,680 per person
$5,680
per person
found 17 hours ago
Prospect Berkshires
3.0-star property

Prospect Berkshires

Jun 11 - Jun 14

3 night stay

Atlanta (ATL) to Albany (ALB)

Delta • Roundtrip • Coach
Price was $1,442, price is now $1,117 per person
$1,117
per person
found 17 hours ago
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Travelers ❤️ These Berkshire County 🏨

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 Tanglewood Music Center and Guido's Marketplace are located nearby.
9/10 Wonderful! (944 reviews)
"The rooms were so spacious, with a great kitchen full of dishware to use. The Staff were so kind, helpful and knowledgeable."

Reviewed on May 21, 2026

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
9/10 Wonderful! (953 reviews)
"Berkshires Untold is an appropriate name for the hotel because the photo I was given when I booked the room was of a different place altogether. False advertising. What we actually got was a room in a MOTEL. It had a filthy rug, a screaming loud AC, a dirty shower and it smelled of must. They couldn’t ..."

Reviewed on May 22, 2026

Opens in a new windowBerkshires Untold
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.
8.8/10 Excellent! (2,362 reviews)
"Nice staff, nice room and facilities. Having stayed there several times happily and will be back again in June. Thanks."

Reviewed on May 22, 2026

Opens in a new windowVacation Village in the Berkshires
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Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MCLA Gallery 51 and North Adams Center are located nearby.
8.8/10 Excellent! (1,002 reviews)
"We liked the art gallery and the community exhibition in the ground floor of the hotel. We also appreciated how easy it was to park on the property. The location was perfect for us; so easy to get to nearby attractions and Williams College."

Reviewed on May 21, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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 $112. 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 June. 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 $112. 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 $112 and $1,195. 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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