Flights To Berkshire County - Cheap Flights Starting at CA $104

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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, Sep 11 - Sat, Sep 12
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $251 Roundtrip, found 9 hours ago
CA $251
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Sep 11 from Orlando Intl. to Bradley Intl., returning Sat, Sep 12, priced at CA $251 found 9 hours ago
Fri, Sep 25 - Mon, Sep 28
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $287 Roundtrip, found 6 days ago
CA $287
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Sep 25 from Orlando Intl. to Bradley Intl., returning Mon, Sep 28, priced at CA $287 found 6 days ago
Fri, Sep 25 - Mon, Sep 28
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $293 Roundtrip, found 6 days ago
CA $293
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Sep 25 from Orlando Intl. to Bradley Intl., returning Mon, Sep 28, priced at CA $293 found 6 days ago
Tue, Aug 4 - Wed, Aug 5
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $297 Roundtrip, found 13 hours ago
CA $297
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Tue, Aug 4 from Orlando Intl. to Bradley Intl., returning Wed, Aug 5, priced at CA $297 found 13 hours ago
Fri, Sep 11 - Sat, Sep 12
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $298 Roundtrip, found 9 hours ago
CA $298
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Sep 11 from Orlando Intl. to Bradley Intl., returning Sat, Sep 12, priced at CA $298 found 9 hours ago
Fri, Sep 25 - Mon, Sep 28
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $302 Roundtrip, found 6 days ago
CA $302
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Sep 25 from Orlando Intl. to Bradley Intl., returning Mon, Sep 28, priced at CA $302 found 6 days ago
Thu, Sep 24 - Mon, Sep 28
MCO
Orlando Intl.
ALB
Albany Intl.
CA $394 Roundtrip, found 6 days ago
CA $394
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, Sep 24 from Orlando Intl. to Albany Intl., returning Mon, Sep 28, priced at CA $394 found 6 days ago
Tue, Sep 1 - Tue, Sep 22
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $582 Roundtrip, found 10 hours ago
CA $582
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Sep 1 from Pearson Intl. to Bradley Intl., returning Tue, Sep 22, priced at CA $582 found 10 hours ago
Sun, Jan 24 - Sat, Feb 6
YUL
Pierre Elliott Trudeau Intl.
ALB
Albany Intl.
CA $658 Roundtrip, found 5 days ago
CA $658
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Jan 24 from Pierre Elliott Trudeau Intl. to Albany Intl., returning Sat, Feb 6, priced at CA $658 found 5 days ago
OriginDestinationTravel datesFlights from*
JFKWindsor LocksJuly 30 to August 2CA $316
RSWWindsor LocksSeptember 24 to September 29CA $320
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKLathamJuly 11 to July 13CA $711
*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

Jul 22 - Jul 26

4 night stay

Toronto (YTO) to Albany (ALB)

Porter Airlines • Roundtrip • Coach
Price was CA $839, price is now CA $666 per person
CA $666
per person
found 1 day ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5-star property

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

Jul 22 - Jul 26

4 night stay

Toronto (YTO) to Albany (ALB)

Porter Airlines • Roundtrip • Coach
Price was CA $1,451, price is now CA $1,138 per person
CA $1,138
per person
found 1 day ago
The Red Lion Inn
3.5-star property

The Red Lion Inn

Jul 22 - Jul 26

4 night stay

Toronto (YTO) to Albany (ALB)

Porter Airlines • Roundtrip • Coach
Price was CA $2,068, price is now CA $1,775 per person
CA $1,775
per person
found 1 day 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.
8.8/10 Excellent! (2,429 reviews)
"We absolutely love it there! Colleen at the front desk has been there a very long time she's sweet as can be! everyone is so nice and helpful, and the place is relaxing and clean we stay there quite often!"

Reviewed on Jul 9, 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! (1,008 reviews)
"Great location with easy parking Excellent cleaning staff. Done promptly and right. Very helpful front desk staff."

Reviewed on Jul 7, 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 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! (1,024 reviews)
"Nice property good coffee"

Reviewed on Jul 6, 2026

Opens in a new windowBerkshire Mountain Lodge
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The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
8.8/10 Excellent! (1,009 reviews)
"Had a lovely 2 night stay at the Red Lion Inn. The front desk staff were very welcoming. The location was convenient to many nice shops and restaurants, as well as sites like the Norman Rockwell museum and the Divine Mercies chapel and grounds. This hotel is a wonderful blend of historic and modern..and ..."

Reviewed on Jul 7, 2026

Opens in a new windowThe Red Lion 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 CA $251. 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 17 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 $251. 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 $251 and CA $711. 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.