Cheap Flights to Berkshire County from $29 (2026/2027)

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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, Apr 2 - Thu, Apr 23
MCO
Orlando Intl.
BDL
Bradley Intl.
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Apr 2 from Orlando Intl. to Bradley Intl., returning Thu, Apr 23, priced at $68 found 2 days ago
Wed, Aug 26 - Wed, Sep 2
JAX
Jacksonville Intl.
BDL
Bradley Intl.
$82 Roundtrip, found 5 days ago
$82
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Jacksonville Intl. to Bradley Intl., returning Wed, Sep 2, priced at $82 found 5 days ago
Wed, Jun 10 - Wed, Jun 17
MCO
Orlando Intl.
BDL
Bradley Intl.
$82 Roundtrip, found 4 days ago
$82
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Jun 10 from Orlando Intl. to Bradley Intl., returning Wed, Jun 17, priced at $82 found 4 days ago
Fri, Jun 5 - Tue, Jun 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$84 Roundtrip, found 19 hours ago
$84
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Fri, Jun 5 from Orlando Intl. to Bradley Intl., returning Tue, Jun 9, priced at $84 found 19 hours ago
Sun, Sep 6 - Fri, Sep 11
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, Sep 6 from Raleigh - Durham Intl. to Albany Intl., returning Fri, Sep 11, priced at $97 found 5 days ago
Mon, Aug 31 - Wed, Sep 9
RDU
Raleigh - Durham Intl.
BDL
Bradley Intl.
$117 Roundtrip, found 20 hours ago
$117
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Mon, Aug 31 from Raleigh - Durham Intl. to Bradley Intl., returning Wed, Sep 9, priced at $117 found 20 hours ago
Wed, Aug 19 - Mon, Aug 24
TPA
Tampa Intl.
BDL
Bradley Intl.
$122 Roundtrip, found 8 hours ago
$122
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from Tampa Intl. to Bradley Intl., returning Mon, Aug 24, priced at $122 found 8 hours ago
Thu, Apr 30 - Tue, May 5
MCO
Orlando Intl.
ALB
Albany Intl.
$132 Roundtrip, found 5 hours ago
$132
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Thu, Apr 30 from Orlando Intl. to Albany Intl., returning Tue, May 5, priced at $132 found 5 hours ago
Wed, May 27 - Mon, Jun 1
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, May 27 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Jun 1, priced at $147 found 4 days ago
Mon, May 11 - Tue, May 12
MCO
Orlando Intl.
ALB
Albany Intl.
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, May 11 from Orlando Intl. to Albany Intl., returning Tue, May 12, priced at $167 found 6 days ago
OriginDestinationTravel DatesFlights From*
RSWLathamMay 23 to May 30$122
JFKWindsor LocksMay 11 to May 18$137
RSWWindsor LocksJune 4 to June 7$152
JFKLathamApril 16 to April 22$189
MANWindsor LocksMarch 24 to March 31$765
MANLathamMay 15 to May 17$1,090
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksMarch 15 to April 5$243
RSWLathamMarch 14 to March 17$298
RSWWindsor LocksMarch 13 to March 17$362
JFKLathamMarch 13 to March 14$618
MANWindsor LocksMarch 14 to March 15$927
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Saratoga Casino Hotel
4.0-star property

Saratoga Casino Hotel

Mar 16 - Mar 19

3 night stay

Orlando (MCO) to Albany (ALB)

Delta • Non-stop • Coach

Albany (ALB) to Orlando (MCO)

Southwest Airlines • Non-stop • Coach
Price was $626, price is now $516 per person
$516
per person
found 1 day ago
The Clocktower Hotel Latham - North Albany, an Ascend Collection Hotel
2.5-star property

The Clocktower Hotel Latham - North Albany, an Ascend Collection Hotel

May 10 - May 16

6 night stay

Orlando (MCO) to Albany (ALB)

Southwest Airlines • Coach

Albany (ALB) to Orlando (MCO)

Delta • Coach
Price was $876, price is now $743 per person
$743
per person
found 10 hours ago
Marriott Albany
3.5-star property

Marriott Albany

Apr 24 - Apr 28

4 night stay

Orlando (MCO) to Albany (ALB)

Southwest Airlines • Non-stop • Coach

Albany (ALB) to Orlando (MCO)

Breeze Airways • Non-stop • Coach
Price was $650, price is now $556 per person
$556
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.
8.8/10 Excellent! (2,285 reviews)
Looks way better in person than the pictures. Still old and dated but not as spooky as the pictures seem. They don't tell you this at all, just expect you to read a packet - there is no housekeeping, no nothing. You are supposed to take your own trash out. They also do not really clean the room beforehand ...

Reviewed on Mar 7, 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.
8.8/10 Excellent! (1,005 reviews)
For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options.

Reviewed on Mar 5, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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! (869 reviews)
The staff at the front desk was welcoming, the room was very nice. We enjoyed our stay. HOWEVER - on the day we were to arrive there was a major blizzard. There was no safe way to drive from the Boston area to Pittsfield. I called the hotel 2 days before to say that we would be arriving a day after ...

Reviewed on Mar 6, 2026

Opens in a new windowBerkshire Mountain Lodge
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The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Williams College Museum of Art and Chapin Library of Rare Books and Manuscripts are located nearby.
9.6/10 Exceptional! (584 reviews)
Lovely boutique hotel next to Williams. Just a light continental breakfast during the winter but there are other spots to find a hearty breakfast in town.

Reviewed on Mar 4, 2026

Opens in a new windowThe Williams 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 $68. 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 18 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 April. 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 $68. 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 $68 and $1,090. 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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