Flights To Berkshire County - Cheap Flights Starting at CA $95

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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, Oct 29 - Mon, Nov 2
TPA
Tampa Intl.
BDL
Bradley Intl.
CA $224 Roundtrip, found 4 days ago
CA $224
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Oct 29 from Tampa Intl. to Bradley Intl., returning Mon, Nov 2, priced at CA $224 found 4 days ago
Thu, Jan 21 - Sun, Jan 24
TPA
Tampa Intl.
ALB
Albany Intl.
CA $232 Roundtrip, found 1 day ago
CA $232
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jan 21 from Tampa Intl. to Albany Intl., returning Sun, Jan 24, priced at CA $232 found 1 day ago
Wed, Nov 11 - Sat, Nov 14
TPA
Tampa Intl.
BDL
Bradley Intl.
CA $237 Roundtrip, found 10 hours ago
CA $237
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Wed, Nov 11 from Tampa Intl. to Bradley Intl., returning Sat, Nov 14, priced at CA $237 found 10 hours ago
Fri, Oct 2 - Mon, Oct 5
TPA
Tampa Intl.
BDL
Bradley Intl.
CA $243 Roundtrip, found 6 days ago
CA $243
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Oct 2 from Tampa Intl. to Bradley Intl., returning Mon, Oct 5, priced at CA $243 found 6 days ago
Thu, Nov 12 - Sun, Nov 15
TPA
Tampa Intl.
BDL
Bradley Intl.
CA $252 Roundtrip, found 1 day ago
CA $252
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 12 from Tampa Intl. to Bradley Intl., returning Sun, Nov 15, priced at CA $252 found 1 day ago
Thu, Nov 12 - Sun, Nov 15
TPA
Tampa Intl.
BDL
Bradley Intl.
CA $255 Roundtrip, found 1 day ago
CA $255
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 12 from Tampa Intl. to Bradley Intl., returning Sun, Nov 15, priced at CA $255 found 1 day ago
Thu, Nov 12 - Sun, Nov 15
TPA
Tampa Intl.
BDL
Bradley Intl.
CA $327 Roundtrip, found 1 day ago
CA $327
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Nov 12 from Tampa Intl. to Bradley Intl., returning Sun, Nov 15, priced at CA $327 found 1 day ago
Fri, Sep 25 - Sun, Sep 27
ORD
O'Hare Intl.
BDL
Bradley Intl.
CA $339 Roundtrip, found 1 day ago
CA $339
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Sep 25 from O'Hare Intl. to Bradley Intl., returning Sun, Sep 27, priced at CA $339 found 1 day ago
Fri, Sep 25 - Sun, Oct 4
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $644 Roundtrip, found 4 hours ago
CA $644
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Sep 25 from Pearson Intl. to Bradley Intl., returning Sun, Oct 4, priced at CA $644 found 4 hours ago
Thu, Sep 10 - Tue, Sep 15
YYZ
Pearson Intl.
ALB
Albany Intl.
CA $662 Roundtrip, found 5 days ago
CA $662
Roundtrip
found 5 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 5 days ago
Wed, Oct 21 - Wed, Nov 18
YVR
Vancouver Intl.
BDL
Bradley Intl.
CA $732 Roundtrip, found 2 days ago
CA $732
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Oct 21 from Vancouver Intl. to Bradley Intl., returning Wed, Nov 18, priced at CA $732 found 2 days ago
OriginDestinationTravel datesFlights from*
RSWLathamOctober 17 to October 24CA $199
RSWWindsor LocksSeptember 10 to September 13CA $339
JFKWindsor LocksSeptember 12 to September 13CA $360
JFKLathamSeptember 29 to October 4CA $463
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
RSWWindsor LocksAugust 29 to August 31CA $486
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 1 day 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 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.
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! (1,019 reviews)
"Room smelled must but was orderly. I found 2 bugs in the bathroom. The water pressure was decent in the shower but did not get very hot. Warm enough though. The breakfast did not taste very good but it was free. Free parking which was nice and a very pretty lake/ look out areas behind the inn with ..."

Reviewed on Aug 24, 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 $199. 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 October. 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 $199. 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 $199 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.