Cheap Flights to Berkshire County from $69 (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 2 days ago
$135
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Jun 9 from Orlando Intl. to Bradley Intl., returning Wed, Jun 10, priced at $135 found 2 days ago
Wed, Aug 26 - Mon, Aug 31
TPA
Tampa Intl.
BDL
Bradley Intl.
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Tampa Intl. to Bradley Intl., returning Mon, Aug 31, priced at $142 found 2 days ago
Wed, Sep 2 - Tue, Sep 8
TPA
Tampa Intl.
BDL
Bradley Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Tue, Sep 8, priced at $142 found 1 day ago
Sat, Jun 6 - Wed, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$147 Roundtrip, found 6 hours ago
$147
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 $147 found 6 hours ago
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$174 Roundtrip, just found
$174
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Sep 3 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 6, priced at $174 just found
Thu, Sep 10 - Wed, Sep 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$182 Roundtrip, found 2 days ago
$182
Roundtrip
found 2 days 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 2 days ago
Mon, Aug 31 - Thu, Sep 3
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$187 Roundtrip, found 4 days ago
$187
Roundtrip
found 4 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 4 days ago
Mon, Aug 24 - Thu, Sep 3
TPA
Tampa Intl.
ALB
Albany Intl.
$189 Roundtrip, found 4 days ago
$189
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Aug 24 from Tampa Intl. to Albany Intl., returning Thu, Sep 3, priced at $189 found 4 days ago
OriginDestinationTravel DatesFlights From*
RSWLathamSeptember 2 to September 9$112
RSWWindsor LocksSeptember 3 to September 6$152
JFKWindsor LocksJune 6 to June 10$202
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
RSWWindsor LocksMay 30 to June 7$220
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.
Berkshire Mountain Lodge
3.0-star property

Berkshire Mountain Lodge

Jul 26 - Jul 30

4 night stay

Tampa (TPA) to Albany (ALB)

American Airlines • Non-stop roundtrip • Coach
Price was $625, price is now $511 per person
$511
per person
found 6 hours ago
Brook Bound Inn
2.0-star property

Brook Bound Inn

May 26 - May 31

5 night stay

Denver (DEN) to Albany (ALB)

Southwest Airlines • Non-stop • Coach

Albany (ALB) to Denver (DEN)

Delta • Non-stop • Coach
Price was $1,541, price is now $1,243 per person
$1,243
per person
found 1 day ago
Vacation Village in the Berkshires
3.0-star property

Vacation Village in the Berkshires

Jul 26 - Jul 30

4 night stay

Tampa (TPA) to Albany (ALB)

American Airlines • Non-stop • Coach

Albany (ALB) to Tampa (TPA)

Breeze Airways • Non-stop • Coach
Price was $782, price is now $654 per person
$654
per person
found 6 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! (946 reviews)
"The stay was great . No complains at all . Definitely will be staying in the near future ."

Reviewed on May 22, 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! (957 reviews)
"Loved my stay here! The staff is friendly and helpful and the property is clean, comfortable and nicely appointed with a small bar and dining area. My room was spotless with an updated and spacious bathroom. The bed and linens were comfortable and there was a cozy reading chair as well. I loved the ..."

Reviewed on May 23, 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.
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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