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.

Sat, Feb 14 - Sun, Feb 22
MCO
Orlando Intl.
BDL
Bradley Intl.
$56 Roundtrip, found 4 hours ago
$56
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Orlando Intl. to Bradley Intl., returning Sun, Feb 22, priced at $56 found 4 hours ago
Sat, Feb 7 - Mon, Feb 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$89 Roundtrip, found 6 hours ago
$89
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sat, Feb 7 from Orlando Intl. to Bradley Intl., returning Mon, Feb 9, priced at $89 found 6 hours ago
Fri, Apr 17 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$102 Roundtrip, found 12 hours ago
$102
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Fri, Apr 17 from Raleigh - Durham Intl. to Albany Intl., returning Mon, Apr 20, priced at $102 found 12 hours ago
Tue, Aug 25 - Wed, Sep 2
RDU
Raleigh - Durham Intl.
BDL
Bradley Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Aug 25 from Raleigh - Durham Intl. to Bradley Intl., returning Wed, Sep 2, priced at $112 found 5 days ago
Tue, Mar 17 - Tue, Mar 17
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$114 Roundtrip, found 1 day ago
$114
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Mar 17 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Mar 17, priced at $114 found 1 day ago
Wed, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$122 Roundtrip, found 3 days ago
$122
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $122 found 3 days ago
Fri, Feb 13 - Tue, Feb 17
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Feb 13 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, Feb 17, priced at $130 found 1 day ago
Thu, Feb 5 - Mon, Feb 9
MCO
Orlando Intl.
ALB
Albany Intl.
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Feb 5 from Orlando Intl. to Albany Intl., returning Mon, Feb 9, priced at $138 just found
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksFebruary 13 to February 18$103
RSWWindsor LocksMarch 5 to March 9$119
RSWLathamApril 28 to April 29$199
JFKLathamFebruary 26 to March 5$248
MANWindsor LocksMarch 2 to March 15$775
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksFebruary 1 to February 2$117
RSWWindsor LocksJanuary 30 to February 2$212
RSWLathamJanuary 31 to February 7$222
JFKLathamJanuary 30 to February 4$315
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Landing Hotel at Rivers Casino & Resort
4.0-star property

The Landing Hotel at Rivers Casino & Resort

Jan 29 - Feb 1

3 night stay

Denver (DEN) to Albany (ALB)

American Airlines • Non-stop • Coach

Albany (ALB) to Denver (DEN)

Southwest Airlines • Non-stop • Coach
Price was $825, price is now $652 per person
$652
per person
found 6 hours ago
Country Inn & Suites by Radisson, Downtown Albany New York
3.0-star property

Country Inn & Suites by Radisson, Downtown Albany New York

Jan 29 - Feb 1

3 night stay

Denver (DEN) to Albany (ALB)

American Airlines • Non-stop • Coach

Albany (ALB) to Denver (DEN)

Southwest Airlines • Non-stop • Coach
Price was $718, price is now $653 per person
$653
per person
found 6 hours ago
Marriott Albany
3.5-star property

Marriott Albany

Jan 29 - Feb 1

3 night stay

Denver (DEN) to Albany (ALB)

American Airlines • Non-stop • Coach

Albany (ALB) to Denver (DEN)

Southwest Airlines • Non-stop • Coach
Price was $761, price is now $699 per person
$699
per person
found 6 hours 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 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! (2,211 reviews)
Room clean staff polite

Reviewed on Jan 18, 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 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! (816 reviews)
Clean, great location near Bosquet Mountain and grocery store, spacious condo, easy.

Reviewed on Jan 19, 2026

Opens in a new windowBerkshire Mountain Lodge
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! (564 reviews)
Great stay. Comfortable hotel and very friendly staff. Restaurant is very good.

Reviewed on Jan 20, 2026

Opens in a new windowThe Williams Inn
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Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
8/10 Very Good! (1,006 reviews)
generally good

Reviewed on Jan 19, 2026

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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 $775. 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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