Flights To Berkshire County - Cheap Flights Starting at CA $68

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Berkshire County's top cities

A town hall with a central dome and columns, surrounded by trees and people.

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 4 - Fri, Dec 11
PIT
Pittsburgh Intl.
BDL
Bradley Intl.
CA $187 Roundtrip, found 6 days ago
CA $187
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Dec 4 from Pittsburgh Intl. to Bradley Intl., returning Fri, Dec 11, priced at CA $187 found 6 days ago
Mon, Aug 3 - Mon, Aug 10
PIT
Pittsburgh Intl.
BDL
Bradley Intl.
CA $244 Roundtrip, found 1 day ago
CA $244
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Aug 3 from Pittsburgh Intl. to Bradley Intl., returning Mon, Aug 10, priced at CA $244 found 1 day ago
Fri, Dec 4 - Fri, Dec 11
PIT
Pittsburgh Intl.
BDL
Bradley Intl.
CA $262 Roundtrip, found 6 days ago
CA $262
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Dec 4 from Pittsburgh Intl. to Bradley Intl., returning Fri, Dec 11, priced at CA $262 found 6 days ago
Fri, Dec 4 - Fri, Dec 11
PIT
Pittsburgh Intl.
BDL
Bradley Intl.
CA $268 Roundtrip, found 6 days ago
CA $268
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Dec 4 from Pittsburgh Intl. to Bradley Intl., returning Fri, Dec 11, priced at CA $268 found 6 days ago
Wed, Aug 5 - Mon, Aug 10
PIT
Pittsburgh Intl.
BDL
Bradley Intl.
CA $272 Roundtrip, found 1 day ago
CA $272
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Aug 5 from Pittsburgh Intl. to Bradley Intl., returning Mon, Aug 10, priced at CA $272 found 1 day ago
Fri, Dec 4 - Fri, Dec 11
PIT
Pittsburgh Intl.
BDL
Bradley Intl.
CA $284 Roundtrip, found 6 days ago
CA $284
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Dec 4 from Pittsburgh Intl. to Bradley Intl., returning Fri, Dec 11, priced at CA $284 found 6 days ago
Fri, Oct 16 - Sun, Oct 18
PIT
Pittsburgh Intl.
ALB
Albany Intl.
CA $560 Roundtrip, found 5 days ago
CA $560
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Oct 16 from Pittsburgh Intl. to Albany Intl., returning Sun, Oct 18, priced at CA $560 found 5 days ago
Tue, Sep 1 - Tue, Sep 22
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $582 Roundtrip, found 1 day ago
CA $582
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 1 from Pearson Intl. to Bradley Intl., returning Tue, Sep 22, priced at CA $582 found 1 day ago
Sun, Aug 16 - Wed, Aug 19
YHZ
Stanfield Intl.
ALB
Albany Intl.
CA $825 Roundtrip, found 1 day ago
CA $825
Roundtrip
found 1 day ago
Select WestJet flight, departing Sun, Aug 16 from Stanfield Intl. to Albany Intl., returning Wed, Aug 19, priced at CA $825 found 1 day ago
OriginDestinationTravel datesFlights from*
JFKWindsor LocksJuly 30 to August 2CA $316
RSWWindsor LocksSeptember 24 to September 29CA $320
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Quality Inn & Suites Schoharie near Howe Caverns
2.5-star property

Quality Inn & Suites Schoharie near Howe Caverns

Jul 24 - Jul 27

3 night stay

Montreal (YMQ) to Albany (ALB)

Porter Airlines • Roundtrip • Coach
Price was CA $852, price is now CA $759 per person
CA $759
per person
found 1 day ago
Countryside Inn
2.5-star property

Countryside Inn

Jul 24 - Jul 27

3 night stay

Montreal (YMQ) to Albany (ALB)

Porter Airlines • Roundtrip • Coach
Price was CA $858, price is now CA $759 per person
CA $759
per person
found 1 day ago
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area
3.0-star property

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

Sep 3 - Sep 8

5 night stay

Toronto (YYZ) to Albany (ALB)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,259, price is now CA $1,126 per person
CA $1,126
per person
found 8 hours ago
Don't see what you're looking for?
See all available trips from Montreal to Berkshire County
View all trips

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! (2,430 reviews)
"Very nice room and facility"

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! (1,010 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."

Reviewed on Jul 9, 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! (1,028 reviews)
"We have stayed at the BML numerous times over a span of four years. We originally found the BML through Expedia and have been returning every time we are in the Berkshires. We keep returning for two simple reasons: #1- the pristine condition of the property and our individual room (and we’ve stayed ..."

Reviewed on Jul 9, 2026

Opens in a new windowBerkshire Mountain Lodge
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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! (1,011 reviews)
"Clean room. Arrived late."

Reviewed on Jul 10, 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 $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 16 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 $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 $825. 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.