Flights To Berkshire County - Cheap Flights Starting at CA $73

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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, Dec 11 - Mon, Dec 14
JAX
Jacksonville Intl.
BDL
Bradley Intl.
CA $145 Roundtrip, found 1 day ago
CA $145
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 11 from Jacksonville Intl. to Bradley Intl., returning Mon, Dec 14, priced at CA $145 found 1 day ago
Fri, Nov 6 - Mon, Nov 9
JAX
Jacksonville Intl.
BDL
Bradley Intl.
CA $202 Roundtrip, found 1 day ago
CA $202
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Nov 6 from Jacksonville Intl. to Bradley Intl., returning Mon, Nov 9, priced at CA $202 found 1 day ago
Fri, Nov 20 - Mon, Nov 30
JAX
Jacksonville Intl.
ALB
Albany Intl.
CA $535 Roundtrip, found 9 hours ago
CA $535
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Fri, Nov 20 from Jacksonville Intl. to Albany Intl., returning Mon, Nov 30, priced at CA $535 found 9 hours ago
Wed, Nov 11 - Thu, Nov 12
YVR
Vancouver Intl.
ALB
Albany Intl.
CA $670 Roundtrip, found 1 day ago
CA $670
Roundtrip
found 1 day ago
Select United flight, departing Wed, Nov 11 from Vancouver Intl. to Albany Intl., returning Thu, Nov 12, priced at CA $670 found 1 day ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $672 Roundtrip, found 1 day ago
CA $672
Roundtrip
found 1 day ago
Select United flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $672 found 1 day ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $672 Roundtrip, found 1 day ago
CA $672
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $672 found 1 day ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $672 Roundtrip, found 1 day ago
CA $672
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $672 found 1 day ago
Wed, Oct 21 - Tue, Oct 27
YYZ
Pearson Intl.
ALB
Albany Intl.
CA $674 Roundtrip, found 1 day ago
CA $674
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 21 from Pearson Intl. to Albany Intl., returning Tue, Oct 27, priced at CA $674 found 1 day ago
OriginDestinationTravel datesFlights from*
RSWLathamOctober 31 to November 4CA $322
RSWWindsor LocksDecember 10 to December 14CA $396
JFKWindsor LocksDecember 5 to December 6CA $449
JFKLathamOctober 22 to October 28CA $515
MANWindsor LocksNovember 29 to December 4CA $1,753
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
RSWLathamOctober 10 to October 17CA $513
JFKWindsor LocksOctober 10 to October 12CA $702
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
The Whitlock
2.0-star property

The Whitlock

Oct 20 - Oct 23

3 night stay

Edmonton (YEG) to Albany (ALB)

Air Canada • Non-stop roundtrip • Coach
Price was CA $980, price is now CA $818 per person
CA $818
per person
found 1 day ago
Hotel On North
3.5-star property

Hotel On North

Oct 20 - Oct 23

3 night stay

Edmonton (YEG) to Albany (ALB)

Air Canada • Non-stop roundtrip • Coach
Price was CA $1,006, price is now CA $844 per person
CA $844
per person
found 1 day ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
3.5-star property

Holiday Inn Club Vacations Oak 'n Spruce Resort

Jan 2 - Jan 5

3 night stay

Toronto (YTO) to Albany (ALB)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $1,080, price is now CA $922 per person
CA $922
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 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! (2,712 reviews)
"Very spacious and clean room , at an affordable price vast of amenities surrounded by nature"

Reviewed on Oct 6, 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 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.
9/10 Wonderful! (1,180 reviews)
"Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well"

Reviewed on Oct 6, 2026

Opens in a new windowBerkshire Mountain Lodge
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
8.6/10 Excellent! (1,000 reviews)
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."

Reviewed on Oct 5, 2026

Opens in a new windowQuality Inn Great Barrington
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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! (1,007 reviews)
"Gave my jacuzzi room, that I paid extra for, away to the wrong person because we had the same first name."

Reviewed on Oct 4, 2026

Opens in a new windowThe Yankee 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 $145. 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 December. 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 $145. 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 $145 and CA $1,753. 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.