Flights To Berkshire County - Cheap Flights Starting at CA $91

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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, Sep 10 - Mon, Sep 14
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $187 Roundtrip, found 4 days ago
CA $187
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Bradley Intl., returning Mon, Sep 14, priced at CA $187 found 4 days ago
Fri, Oct 2 - Mon, Oct 5
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $201 Roundtrip, found 3 days ago
CA $201
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Oct 2 from Orlando Intl. to Bradley Intl., returning Mon, Oct 5, priced at CA $201 found 3 days ago
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
CA $226 Roundtrip, found 15 hours ago
CA $226
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 6, priced at CA $226 found 15 hours ago
Fri, Oct 2 - Tue, Oct 6
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
CA $246 Roundtrip, found 3 days ago
CA $246
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Oct 2 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Oct 6, priced at CA $246 found 3 days ago
Fri, Oct 23 - Sun, Oct 25
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
CA $301 Roundtrip, found 4 days ago
CA $301
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, Oct 23 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Oct 25, priced at CA $301 found 4 days ago
Thu, Dec 3 - Sun, Dec 6
MCO
Orlando Intl.
ALB
Albany Intl.
CA $302 Roundtrip, found 10 hours ago
CA $302
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Albany Intl., returning Sun, Dec 6, priced at CA $302 found 10 hours ago
Thu, Oct 15 - Mon, Oct 19
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $365 Roundtrip, found 4 days ago
CA $365
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Oct 15 from Orlando Intl. to Bradley Intl., returning Mon, Oct 19, priced at CA $365 found 4 days ago
Sat, Sep 12 - Mon, Sep 14
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $365 Roundtrip, found 6 days ago
CA $365
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Sep 12 from Orlando Intl. to Bradley Intl., returning Mon, Sep 14, priced at CA $365 found 6 days ago
Thu, Sep 10 - Tue, Sep 15
YYZ
Pearson Intl.
ALB
Albany Intl.
CA $662 Roundtrip, found 4 days ago
CA $662
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Sep 10 from Pearson Intl. to Albany Intl., returning Tue, Sep 15, priced at CA $662 found 4 days ago
Sat, Sep 26 - Tue, Sep 29
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $687 Roundtrip, found 2 days ago
CA $687
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 26 from Pearson Intl. to Bradley Intl., returning Tue, Sep 29, priced at CA $687 found 2 days ago
Wed, Oct 21 - Wed, Nov 18
YVR
Vancouver Intl.
BDL
Bradley Intl.
CA $732 Roundtrip, found 1 day ago
CA $732
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Oct 21 from Vancouver Intl. to Bradley Intl., returning Wed, Nov 18, priced at CA $732 found 1 day ago
OriginDestinationTravel datesFlights from*
RSWLathamOctober 17 to October 24CA $199
RSWWindsor LocksSeptember 10 to September 13CA $339
JFKWindsor LocksSeptember 17 to September 20CA $355
JFKLathamSeptember 29 to October 4CA $463
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKWindsor LocksAugust 29 to September 13CA $515
*Prices include taxes and fees
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

Sep 26 - Oct 2

6 night stay

Toronto (YYZ) to Albany (ALB)

Porter Airlines • Roundtrip • Coach
Price was CA $1,037, price is now CA $788 per person
CA $788
per person
found 13 hours ago
Berkshire Mountain Lodge
3.0-star property

Berkshire Mountain Lodge

Oct 6 - Oct 11

5 night stay

Toronto (YYZ) to Albany (ALB)

Porter Airlines • Roundtrip • Coach
Price was CA $1,242, price is now CA $920 per person
CA $920
per person
found 1 day ago
Hideaway Inn Lenox
2.0-star property

Hideaway Inn Lenox

Sep 26 - Oct 2

6 night stay

Toronto (YYZ) to Albany (ALB)

Porter Airlines • Roundtrip • Coach
Price was CA $1,722, price is now CA $1,358 per person
CA $1,358
per person
found 13 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 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.
8.8/10 Excellent! (2,556 reviews)
"Price - quality =awesome"

Reviewed on Aug 22, 2026

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! (1,018 reviews)
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."

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.
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 CA $187. 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 20 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 September. 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 CA $187. 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 CA $187 and CA $732. 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.