Cheap Flights to Berkshire County from $28 (2026/2027)

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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, Feb 5 - Sun, Feb 8
MCO
Orlando Intl.
BDL
Bradley Intl.
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Feb 5 from Orlando Intl. to Bradley Intl., returning Sun, Feb 8, priced at $56 found 1 hour ago
Thu, Jan 29 - Sat, Jan 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$59 Roundtrip, found 5 days ago
$59
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Jan 29 from Orlando Intl. to Bradley Intl., returning Sat, Jan 31, priced at $59 found 5 days ago
Sun, Jan 25 - Tue, Jan 27
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$97 Roundtrip, found 5 days ago
$97
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Jan 25 from Raleigh - Durham Intl. to Albany Intl., returning Tue, Jan 27, priced at $97 found 5 days ago
Fri, Feb 27 - Mon, Mar 2
TPA
Tampa Intl.
BDL
Bradley Intl.
$107 Roundtrip, found 11 hours ago
$107
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Feb 27 from Tampa Intl. to Bradley Intl., returning Mon, Mar 2, priced at $107 found 11 hours ago
Wed, Feb 4 - Sun, Feb 8
RDU
Raleigh - Durham Intl.
BDL
Bradley Intl.
$112 Roundtrip, found 1 hour ago
$112
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Feb 4 from Raleigh - Durham Intl. to Bradley Intl., returning Sun, Feb 8, priced at $112 found 1 hour ago
Thu, Jan 29 - Mon, Feb 9
MCO
Orlando Intl.
ALB
Albany Intl.
$128 Roundtrip, found 3 days ago
$128
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jan 29 from Orlando Intl. to Albany Intl., returning Mon, Feb 9, priced at $128 found 3 days ago
Thu, Mar 26 - Sun, Mar 29
MCO
Orlando Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Mar 26 from Orlando Intl. to Bradley Intl., returning Sun, Mar 29, priced at $137 found 1 day ago
Thu, Feb 26 - Sat, Feb 28
MCO
Orlando Intl.
BDL
Bradley Intl.
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Feb 26 from Orlando Intl. to Bradley Intl., returning Sat, Feb 28, priced at $138 found 1 day ago
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksFebruary 19 to February 23$110
RSWWindsor LocksFebruary 2 to February 5$163
RSWLathamJanuary 28 to February 3$184
JFKLathamApril 7 to April 15$311
MANLathamFebruary 23 to March 2$860
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksJanuary 18 to January 26$193
RSWWindsor LocksJanuary 16 to January 20$248
RSWLathamJanuary 17 to January 24$393
JFKLathamJanuary 17 to January 21$469
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

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

Jan 24 - Jan 26

2 night stay

Denver (DEN) to Albany (ALB)

Frontier Airlines • Non-stop • Coach

Albany (ALB) to Denver (DEN)

Southwest Airlines • Non-stop • Coach
Price was $306, price is now $249 per person
$249
per person
found 1 day ago
The Landing Hotel at Rivers Casino & Resort
4.0-star property

The Landing Hotel at Rivers Casino & Resort

Feb 26 - Mar 1

3 night stay

Denver (DEN) to Albany (ALB)

Southwest Airlines • Roundtrip • Coach
Price was $647, price is now $525 per person
$525
per person
found 1 day ago
The White House Inn
3.5-star property

The White House Inn

Mar 25 - Mar 28

3 night stay

Orlando (MCO) to Albany (ALB)

Southwest Airlines • Roundtrip • Coach
Price was $614, price is now $516 per person
$516
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.
8.6/10 Excellent! (2,205 reviews)
The amount of space and super comfortable bed was such a pleasure!

Reviewed on Jan 13, 2026

Opens in a new windowVacation Village in the Berkshires
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.
8.6/10 Excellent! (1,002 reviews)
Staff were good and the room was clean. Bed is comfortable and room is fairly large. Couch is uncomfortable for prolonged sitting. Not having a cafe/restaurant open Tuesdays and Wednesdays or any breakfast bar is a bit inconvenient but there are other local options. Site location makes for some traffic ...

Reviewed on Jan 8, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
8/10 Very Good! (1,006 reviews)
Staff was very courteous and rooms clean.

Reviewed on Jan 12, 2026

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

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 Guido's Marketplace and Bousquet Ski Area are located nearby.
9/10 Wonderful! (1,000 reviews)
Everything was great!

Reviewed on Jan 8, 2026

Opens in a new windowThe Yankee, Trademark Collection by Wyndham
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 $56. 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 February. 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 $56. 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 $56 and $860. 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.
How long is the average flight to Berkshire County?
To get an idea of the average airborne time of a direct flight to Berkshire County, browse through these top routes:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 15 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 9 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 1 hour and 12 minutes

What can I expect on a flight to Berkshire County?
How long your flight takes and whether you're traveling with a low-cost or full-service airline will mostly determine this. If you're searching for long-haul flights to Berkshire County, drinks, meals and entertainment should come as standard. Want cheap flights for family vacations? Look into the deals from budget carriers. Normally, these airlines don't offer as many inclusions, so be prepared to pay for your drinks and meals.

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