Cheap Flights to Berkshire County from $52 (2026/2027)

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Lenox which includes an administrative buidling

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, Apr 30 - Thu, Apr 30
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$96 Roundtrip, found 3 days ago
$96
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Thu, Apr 30, priced at $96 found 3 days ago
Mon, Jun 8 - Wed, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Jun 8 from Orlando Intl. to Bradley Intl., returning Wed, Jun 10, priced at $110 found 2 days ago
Tue, Aug 18 - Tue, Aug 25
MCO
Orlando Intl.
BDL
Bradley Intl.
$142 Roundtrip, found 22 hours ago
$142
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Tue, Aug 18 from Orlando Intl. to Bradley Intl., returning Tue, Aug 25, priced at $142 found 22 hours ago
Fri, Aug 28 - Sun, Sep 6
TPA
Tampa Intl.
BDL
Bradley Intl.
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Aug 28 from Tampa Intl. to Bradley Intl., returning Sun, Sep 6, priced at $147 found 6 days ago
Thu, May 7 - Sun, May 10
MCO
Orlando Intl.
ALB
Albany Intl.
$155 Roundtrip, found 6 days ago
$155
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, May 7 from Orlando Intl. to Albany Intl., returning Sun, May 10, priced at $155 found 6 days ago
Fri, May 1 - Sun, May 3
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$176 Roundtrip, found 5 hours ago
$176
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, May 1 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sun, May 3, priced at $176 found 5 hours ago
Wed, May 6 - Sat, May 23
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$176 Roundtrip, found 10 hours ago
$176
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Wed, May 6 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sat, May 23, priced at $176 found 10 hours ago
Thu, May 7 - Sun, May 10
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$194 Roundtrip, found 21 hours ago
$194
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Thu, May 7 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sun, May 10, priced at $194 found 21 hours ago
OriginDestinationTravel DatesFlights From*
RSWLathamJune 6 to June 13$134
RSWWindsor LocksMay 17 to May 26$175
JFKWindsor LocksApril 30 to May 4$197
JFKLathamApril 16 to April 22$285
MANWindsor LocksApril 29 to May 19$848
MANLathamMay 20 to May 27$1,200
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWLathamMarch 28 to April 1$300
RSWWindsor LocksMarch 27 to March 29$403
JFKWindsor LocksMarch 27 to March 29$413
JFKLathamMarch 27 to March 28$833
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Hotel Saratoga, an Ascend Collection Hotel
3.0-star property

The Hotel Saratoga, an Ascend Collection Hotel

Mar 27 - Mar 30

3 night stay

Green Bay (GRB) to Albany (ALB)

Delta • Non-stop roundtrip • Coach
Price was $662, price is now $626 per person
$626
per person
found 1 day ago
Hotel Brookmere & Arbor Spa
4.0-star property

Hotel Brookmere & Arbor Spa

Mar 27 - Mar 30

3 night stay

Green Bay (GRB) to Albany (ALB)

Delta • Non-stop roundtrip • Coach
Price was $731, price is now $664 per person
$664
per person
found 1 day ago
Comfort Inn & Suites East Greenbush - Albany
2.5-star property

Comfort Inn & Suites East Greenbush - Albany

Mar 27 - Mar 30

3 night stay

Green Bay (GRB) to Albany (ALB)

Delta • Non-stop roundtrip • Coach
Price was $691, price is now $638 per person
$638
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Green Bay to Berkshire County
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Travelers ❤️ These Berkshire County 🏨

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! (1,004 reviews)
Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The ...

Reviewed on Mar 22, 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 Tanglewood Music Center and Guido's Marketplace are located nearby.
9/10 Wonderful! (884 reviews)
This is our 3rd year staying here for my son’s birthday in March. Affordable and having the 2 rooms with a kitchen is so nice. My son’s favorite part is the pool which is always warm and clean, never smells too strong like some places. Hot tub feels amazing too. Will be back next year, or sooner ...

Reviewed on Mar 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! (880 reviews)
Wonderful place, great toiletries and great friendly staff. We will be back

Reviewed on Mar 22, 2026

Opens in a new windowBerkshires Untold
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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
9/10 Wonderful! (856 reviews)
Great place to enjoy with the whole family!!!

Reviewed on Mar 23, 2026

Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the 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 $96. 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 April. 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 $96. 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 $96 and $1,200. 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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