Cheap Flights to Berkshire County from $66 (2026/2027)

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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, Aug 29 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$133 Roundtrip, found 5 days ago
$133
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $133 found 5 days ago
Sat, Aug 29 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $137 found 5 days ago
Wed, Aug 26 - Tue, Sep 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$138 Roundtrip, found 21 hours ago
$138
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Orlando Intl. to Bradley Intl., returning Tue, Sep 1, priced at $138 found 21 hours ago
Wed, Aug 26 - Tue, Sep 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$140 Roundtrip, found 20 hours ago
$140
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from Orlando Intl. to Bradley Intl., returning Tue, Sep 1, priced at $140 found 20 hours ago
Tue, Sep 1 - Mon, Sep 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$141 Roundtrip, found 5 days ago
$141
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Bradley Intl., returning Mon, Sep 7, priced at $141 found 5 days ago
Sun, Aug 30 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$150 Roundtrip, found 14 hours ago
$150
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Sun, Aug 30 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 6, priced at $150 found 14 hours ago
Sat, Sep 12 - Sun, Sep 13
TPA
Tampa Intl.
BDL
Bradley Intl.
$151 Roundtrip, found 18 hours ago
$151
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Sat, Sep 12 from Tampa Intl. to Bradley Intl., returning Sun, Sep 13, priced at $151 found 18 hours ago
Thu, Sep 10 - Wed, Sep 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$163 Roundtrip, found 23 hours ago
$163
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Wed, Sep 16, priced at $163 found 23 hours ago
OriginDestinationTravel DatesFlights From*
RSWLathamSeptember 9 to September 16$102
RSWWindsor LocksSeptember 5 to September 6$132
JFKWindsor LocksSeptember 15 to September 17$207
JFKLathamJuly 25 to July 31$295
MANWindsor LocksAugust 13 to August 26$895
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksJuly 11 to July 13$361
RSWWindsor LocksJuly 11 to July 14$378
RSWLathamJuly 12 to July 16$546
MANWindsor LocksJuly 10 to July 24$1,067
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Vervana, Trademark Collection by Wyndham
2.5-star property

Hotel Vervana, Trademark Collection by Wyndham

Sep 17 - Sep 24

7 night stay

Orlando (MCO) to Albany (ALB)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $981, price is now $767 per person
$767
per person
found 16 hours ago
Brook Bound Inn
2.0-star property

Brook Bound Inn

Sep 17 - Sep 24

7 night stay

Orlando (MCO) to Albany (ALB)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,429, price is now $1,119 per person
$1,119
per person
found 16 hours ago
The White House Inn
3.5-star property

The White House Inn

Sep 17 - Sep 24

7 night stay

Orlando (MCO) to Albany (ALB)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,264, price is now $1,020 per person
$1,020
per person
found 16 hours ago
Don't see what you're looking for?
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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! (2,421 reviews)
"Vacation Villas in the Berkshires was a tremendous property. The facility was spectacular, the rooms clean, great and comfortable and the staff was so friendly and accommodating. We had the best time and I can't wait to go back."

Reviewed on Jul 6, 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! (1,004 reviews)
"Vert clean, incluses breakfast so so"

Reviewed on Jul 6, 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! (1,023 reviews)
"This was a great place to stay. It was clean and quiet. The staff were really helpful And friendly. Although the decor is a bit dated the room was clean and comfortable. There a big kitchen (for a hotel), dining table, sitting room, separate bedroom And a big bathroom. The property also had a large ..."

Reviewed on Jul 6, 2026

Opens in a new windowBerkshire Mountain Lodge
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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! (1,005 reviews)
"We had a window air conditioner that started moaning in the middle of the night - as we were on the 4th floor room was warm! The sink faucet would not stop dripping, the bath tub plug leaked. When we mentioned this to the young staff person at checkout counter she wrote down the issues but offered ..."

Reviewed on Jul 6, 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 $102. 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 August. 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 $102. 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 $102 and $1,067. 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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