Cheap Flights to Berkshire County from $28 (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, Feb 26 - Mon, Mar 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$56 Roundtrip, found 3 hours ago
$56
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Orlando Intl. to Bradley Intl., returning Mon, Mar 2, priced at $56 found 3 hours ago
Sun, Sep 6 - Thu, Sep 10
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Sep 6 from Raleigh - Durham Intl. to Albany Intl., returning Thu, Sep 10, priced at $97 found 2 days ago
Wed, Sep 2 - Tue, Sep 15
RDU
Raleigh - Durham Intl.
BDL
Bradley Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Raleigh - Durham Intl. to Bradley Intl., returning Tue, Sep 15, priced at $112 found 5 days ago
Fri, Mar 6 - Mon, Mar 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$131 Roundtrip, just found
$131
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Mar 6 from Tampa Intl. to Bradley Intl., returning Mon, Mar 9, priced at $131 just found
Thu, Apr 2 - Sat, Apr 11
MCO
Orlando Intl.
ALB
Albany Intl.
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Apr 2 from Orlando Intl. to Albany Intl., returning Sat, Apr 11, priced at $131 found 1 day ago
Sat, May 30 - Sat, Jun 6
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 2 days ago
$137
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 $137 found 2 days ago
Tue, May 19 - Tue, Jun 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, May 19 from Orlando Intl. to Bradley Intl., returning Tue, Jun 2, priced at $137 just found
Wed, Mar 11 - Mon, Mar 16
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$146 Roundtrip, found 6 days ago
$146
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Mar 11 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Mon, Mar 16, priced at $146 found 6 days ago
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksFebruary 21 to February 23$100
RSWWindsor LocksMarch 6 to March 9$147
RSWLathamApril 18 to April 25$214
JFKLathamFebruary 26 to March 4$271
MANWindsor LocksMarch 5 to March 18$820
MANLathamMarch 4 to March 18$991
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksFebruary 15 to February 19$183
RSWWindsor LocksFebruary 14 to March 2$223
RSWLathamFebruary 14 to February 19$290
JFKLathamFebruary 15 to February 16$746
MANWindsor LocksFebruary 15 to February 19$1,402
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

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

The Wiltwyck

Mar 13 - Mar 15

2 night stay

San Juan (SJU) to Albany (ALB)

JetBlue Airways • Roundtrip • Coach
Price was $554, price is now $476 per person
$476
per person
found 11 hours ago
The Landing Hotel at Rivers Casino & Resort
4.0-star property

The Landing Hotel at Rivers Casino & Resort

Feb 27 - Mar 2

3 night stay

Atlanta (ATL) to Albany (ALB)

Delta • Roundtrip • Coach
Price was $746, price is now $544 per person
$544
per person
found 1 day ago
Saratoga Casino Hotel
4.0-star property

Saratoga Casino Hotel

Apr 2 - Apr 5

3 night stay

San Juan (SJU) to Albany (ALB)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $804, price is now $668 per person
$668
per person
found 1 day 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 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! (2,221 reviews)
Everything was great, the staff, the room, and the amenities. We will be coming back.

Reviewed on Jan 25, 2026

Opens in a new windowVacation Village in the Berkshires
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! (1,003 reviews)
Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel.

Reviewed on Feb 1, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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! (826 reviews)
Room was clean and nicely equipped with kitchen. Will return if the future.

Reviewed on Feb 1, 2026

Opens in a new windowBerkshire Mountain Lodge
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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! (572 reviews)
Clean

Reviewed on Jan 31, 2026

Opens in a new windowThe Williams 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 $56. 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 February. 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 $56. 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 $56 and $1,402. 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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