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.

Fri, Jan 22 - Mon, Jan 25
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$98 Roundtrip, found 6 hours ago
$98
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Fri, Jan 22 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Mon, Jan 25, priced at $98 found 6 hours ago
Mon, Dec 7 - Sun, Dec 13
RIC
Richmond Intl.
BDL
Bradley Intl.
$102 Roundtrip, found 8 hours ago
$102
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Mon, Dec 7 from Richmond Intl. to Bradley Intl., returning Sun, Dec 13, priced at $102 found 8 hours ago
Fri, Jan 22 - Mon, Jan 25
PIE
St. Petersburg-Clearwater Intl.
ALB
Albany Intl.
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Fri, Jan 22 from St. Petersburg-Clearwater Intl. to Albany Intl., returning Mon, Jan 25, priced at $102 found 2 days ago
Fri, Jan 8 - Mon, Jan 11
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$151 Roundtrip, found 2 days ago
$151
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 8 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Jan 11, priced at $151 found 2 days ago
Thu, Jan 7 - Sun, Jan 17
TPA
Tampa Intl.
ALB
Albany Intl.
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jan 7 from Tampa Intl. to Albany Intl., returning Sun, Jan 17, priced at $157 found 3 days ago
Wed, Feb 3 - Sun, Feb 7
TPA
Tampa Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 21 hours ago
$161
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Wed, Feb 3 from Tampa Intl. to Bradley Intl., returning Sun, Feb 7, priced at $161 found 21 hours ago
Fri, Dec 4 - Mon, Dec 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$173 Roundtrip, found 13 hours ago
$173
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Bradley Intl., returning Mon, Dec 7, priced at $173 found 13 hours ago
Fri, Jan 22 - Sun, Jan 31
MCO
Orlando Intl.
ALB
Albany Intl.
$175 Roundtrip, found 8 hours ago
$175
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Jan 22 from Orlando Intl. to Albany Intl., returning Sun, Jan 31, priced at $175 found 8 hours ago
OriginDestinationTravel DatesFlights From*
RSWLathamJanuary 8 to January 16$137
JFKWindsor LocksDecember 5 to December 12$157
RSWWindsor LocksJanuary 26 to January 31$173
JFKLathamDecember 4 to December 10$325
MANLathamJanuary 12 to January 27$1,136
MANWindsor LocksFebruary 13 to February 19$1,206
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksNovember 21 to November 24$266
RSWLathamNovember 21 to November 28$287
RSWWindsor LocksNovember 22 to November 28$346
JFKLathamNovember 20 to November 23$451
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Kinsley
3.5-star property

Hotel Kinsley

Dec 27 - Jan 2

6 night stay

San Juan (SJU) to Albany (ALB)

Delta • Coach

Albany (ALB) to San Juan (SJU)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,580, price is now $1,220 per person
$1,220
per person
found 12 hours ago
Luxury Private Estate w Pool Near Rhinebeck
2.0-star property

Luxury Private Estate w Pool Near Rhinebeck

Dec 27 - Jan 2

6 night stay

San Juan (SJU) to Albany (ALB)

Delta • Coach

Albany (ALB) to San Juan (SJU)

Frontier Airlines • Coach
Save 100% on your flight
Price was $11,705, price is now $9,710 per person
$9,710
per person
found 12 hours ago
Brook Bound Inn
2.0-star property

Brook Bound Inn

Jan 1 - Jan 6

5 night stay

San Juan (SJU) to Albany (ALB)

American Airlines • Non-stop • Coach

Albany (ALB) to San Juan (SJU)

United • Non-stop • Coach
Price was $1,617, price is now $1,360 per person
$1,360
per person
found 16 hours ago
Don't see what you're looking for?
See all available trips from San Juan 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 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 Cricket Triple are located nearby.
8.8/10 Excellent! (2,853 reviews)
"Big place,nice indoor pool with arcade. Fireplace in the suite and nice balcony on 2nd floor units. Really close to Jimney Peak"

Reviewed on Nov 15, 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 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
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
Opens in a new windowQuality Inn Great Barrington
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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! (1,004 reviews)
"Everything about this place was wonderful! The location, the staff, the cleanliness. The only downsize was we booked this property because of the pool and it was under maintenance during my stay. A notice would have been nice :( Other than that, beautiful inn."

Reviewed on Nov 14, 2026

Opens in a new windowThe Yankee Inn
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 $98. 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 January. 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 $98. 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 $98 and $1,206. 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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