Flights To Berkshire County - Cheap Flights Starting at CA $96

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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.

Sat, Jun 6 - Wed, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $198 Roundtrip, found 11 hours ago
CA $198
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sat, Jun 6 from Orlando Intl. to Bradley Intl., returning Wed, Jun 10, priced at CA $198 found 11 hours ago
Fri, Jun 5 - Mon, Jun 8
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $218 Roundtrip, found 2 days ago
CA $218
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 5 from Orlando Intl. to Bradley Intl., returning Mon, Jun 8, priced at CA $218 found 2 days ago
Fri, Jun 5 - Mon, Jun 8
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $222 Roundtrip, found 2 days ago
CA $222
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 5 from Orlando Intl. to Bradley Intl., returning Mon, Jun 8, priced at CA $222 found 2 days ago
Fri, Jun 5 - Mon, Jun 8
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $225 Roundtrip, found 2 days ago
CA $225
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 5 from Orlando Intl. to Bradley Intl., returning Mon, Jun 8, priced at CA $225 found 2 days ago
Fri, Jun 5 - Mon, Jun 8
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $229 Roundtrip, found 2 days ago
CA $229
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 5 from Orlando Intl. to Bradley Intl., returning Mon, Jun 8, priced at CA $229 found 2 days ago
Fri, Jun 5 - Tue, Jun 9
MCO
Orlando Intl.
ALB
Albany Intl.
CA $291 Roundtrip, found 3 days ago
CA $291
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Fri, Jun 5 from Orlando Intl. to Albany Intl., returning Tue, Jun 9, priced at CA $291 found 3 days ago
Fri, Jun 5 - Mon, Jun 8
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $326 Roundtrip, found 2 days ago
CA $326
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jun 5 from Orlando Intl. to Bradley Intl., returning Mon, Jun 8, priced at CA $326 found 2 days ago
Tue, Aug 25 - Tue, Sep 1
SAN
San Diego Intl.
BDL
Bradley Intl.
CA $332 Roundtrip, found 2 days ago
CA $332
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Aug 25 from San Diego Intl. to Bradley Intl., returning Tue, Sep 1, priced at CA $332 found 2 days ago
Fri, Jun 12 - Fri, Jun 19
YYZ
Pearson Intl.
ALB
Albany Intl.
CA $640 Roundtrip, found 4 days ago
CA $640
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Jun 12 from Pearson Intl. to Albany Intl., returning Fri, Jun 19, priced at CA $640 found 4 days ago
Wed, Jun 10 - Sat, Jun 20
YYC
Calgary Intl.
ALB
Albany Intl.
CA $666 Roundtrip, found 1 day ago
CA $666
Roundtrip
found 1 day ago
Select WestJet flight, departing Wed, Jun 10 from Calgary Intl. to Albany Intl., returning Sat, Jun 20, priced at CA $666 found 1 day ago
Wed, Aug 12 - Wed, Aug 19
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $711 Roundtrip, found 1 day ago
CA $711
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 12 from Pearson Intl. to Bradley Intl., returning Wed, Aug 19, priced at CA $711 found 1 day ago
OriginDestinationTravel datesFlights from*
JFKWindsor LocksJune 7 to June 10CA $269
RSWWindsor LocksJuly 28 to August 4CA $375
RSWLathamJuly 10 to July 17CA $801
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
RSWWindsor LocksMay 30 to May 31CA $308
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Country Inn & Suites by Radisson, Downtown Albany New York
3.0-star property

Country Inn & Suites by Radisson, Downtown Albany New York

Aug 20 - Aug 25

5 night stay

Toronto (YTO) to Albany (ALB)

Delta • Non-stop roundtrip • Coach
Price was CA $1,344, price is now CA $1,117 per person
CA $1,117
per person
found 12 hours ago
The Landing Hotel at Rivers Casino Schenectady
4.0-star property

The Landing Hotel at Rivers Casino Schenectady

Aug 20 - Aug 25

5 night stay

Toronto (YTO) to Albany (ALB)

Delta • Non-stop roundtrip • Coach
Price was CA $1,727, price is now CA $1,406 per person
CA $1,406
per person
found 12 hours ago
Hampton Inn Albany-Wolf Road (Airport)
2.5-star property

Hampton Inn Albany-Wolf Road (Airport)

Aug 20 - Aug 25

5 night stay

Toronto (YTO) to Albany (ALB)

Delta • Non-stop roundtrip • Coach
Price was CA $1,430, price is now CA $1,182 per person
CA $1,182
per person
found 12 hours ago
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Travelers ❤️ These Berkshire County 🏨

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! (946 reviews)
"The stay was great . No complains at all . Definitely will be staying in the near future ."

Reviewed on May 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! (958 reviews)
"The hotel was funky is a good way, I liked the design and layout of the room and the dining area."

Reviewed on May 23, 2026

Opens in a new windowBerkshires Untold
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! (2,364 reviews)
"The room was clean and spacious. The kitchen was equipped with all necessary supplies to cook a full meal. Great place to stay and relax or plan family fun!"

Reviewed on May 24, 2026

Opens in a new windowVacation Village in the Berkshires
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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! (1,003 reviews)
"I loved the use of space for local artists to display there art. Beautiful work. The hotel was very clean. Loved that you could get a coffee or water throughout the day. I wish that the pool was opened all day. Ample parking"

Reviewed on May 23, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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 $198. 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 June. 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 $198. 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 $198 and CA $801. 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.