Cheap Flights to Berkshire County from $49 (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.

Thu, Nov 5 - Thu, Nov 12
SFB
Orlando Sanford Intl.
ALB
Albany Intl.
$90 Roundtrip, found 5 hours ago
$90
Roundtrip
found 5 hours ago
Select Allegiant Air flight, departing Thu, Nov 5 from Orlando Sanford Intl. to Albany Intl., returning Thu, Nov 12, priced at $90 found 5 hours ago
Fri, Dec 4 - Mon, Dec 7
PIE
St. Petersburg-Clearwater Intl.
ALB
Albany Intl.
$92 Roundtrip, found 6 days ago
$92
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Dec 4 from St. Petersburg-Clearwater Intl. to Albany Intl., returning Mon, Dec 7, priced at $92 found 6 days ago
Thu, Oct 1 - Sun, Oct 4
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$98 Roundtrip, found 5 hours ago
$98
Roundtrip
found 5 hours ago
Select Allegiant Air flight, departing Thu, Oct 1 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Oct 4, priced at $98 found 5 hours ago
Wed, Sep 2 - Sat, Sep 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Orlando Intl. to Bradley Intl., returning Sat, Sep 12, priced at $137 found 4 days ago
Thu, Sep 10 - Mon, Sep 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$138 Roundtrip, found 5 hours ago
$138
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Bradley Intl., returning Mon, Sep 14, priced at $138 found 5 hours ago
Thu, Oct 29 - Wed, Nov 4
TPA
Tampa Intl.
BDL
Bradley Intl.
$147 Roundtrip, found 7 hours ago
$147
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, Oct 29 from Tampa Intl. to Bradley Intl., returning Wed, Nov 4, priced at $147 found 7 hours ago
Thu, Sep 10 - Sat, Sep 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$151 Roundtrip, found 3 days ago
$151
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Sep 10 from Orlando Intl. to Bradley Intl., returning Sat, Sep 12, priced at $151 found 3 days ago
Thu, Sep 10 - Sat, Sep 12
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sat, Sep 12, priced at $159 found 5 days ago
Thu, Jan 21 - Thu, Jan 28
TPA
Tampa Intl.
ALB
Albany Intl.
$176 Roundtrip, found 13 hours ago
$176
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Thu, Jan 21 from Tampa Intl. to Albany Intl., returning Thu, Jan 28, priced at $176 found 13 hours ago
OriginDestinationTravel DatesFlights From*
RSWLathamOctober 21 to October 24$142
RSWWindsor LocksSeptember 29 to October 3$174
JFKWindsor LocksSeptember 21 to September 23$257
JFKLathamOctober 16 to October 22$279
MANWindsor LocksSeptember 11 to January 18$1,047
MANLathamSeptember 14 to September 29$1,087
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWWindsor LocksAugust 30 to September 1$317
RSWLathamAugust 29 to August 30$506
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
3.0-star property

Vacation Village in the Berkshires

Nov 5 - Nov 8

3 night stay

San Juan (SJU) to Albany (ALB)

JetBlue Airways • Roundtrip • Coach
Price was $515, price is now $426 per person
$426
per person
found 1 day ago
The Whitlock
2.0-star property

The Whitlock

Oct 29 - Nov 2

4 night stay

San Juan (SJU) to Albany (ALB)

JetBlue Airways • Roundtrip • Coach
Price was $856, price is now $644 per person
$644
per person
found 1 day ago
Berkshire Mountain Lodge
3.0-star property

Berkshire Mountain Lodge

Oct 29 - Nov 2

4 night stay

San Juan (SJU) to Albany (ALB)

JetBlue Airways • Roundtrip • Coach
Price was $621, price is now $493 per person
$493
per person
found 1 day ago
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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 aparthotel 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.
Opens in a new windowVacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

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 Tanglewood Music Center and Guido's Marketplace are located nearby.
9.2/10 Wonderful! (1,017 reviews)
"I thought the flowers were wood not carpet. We thought we would stay in the main building like last time. Funny smell when we first got there but I opened windows and it was better."

Reviewed on Aug 22, 2026

Opens in a new windowThe Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel 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.
Opens in a new windowBerkshire Mountain Lodge
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FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking and Crane Museum of Papermaking are located nearby.
5.4/10 (883 reviews)
"The exterior was in disarray but the rooms were surprisingly clean!"

Reviewed on Aug 22, 2026

Opens in a new windowFairBridge Inn Express
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 $90. 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 17 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 November. 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 $90. 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 $90 and $1,087. 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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