Cheap Flights to Berkshire County from $60 (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.

Fri, Jan 22 - Mon, Jan 25
PIE
St. Petersburg-Clearwater Intl.
ALB
Albany Intl.
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Jan 22 from St. Petersburg-Clearwater Intl. to Albany Intl., returning Mon, Jan 25, priced at $116 found 1 day ago
Fri, Dec 4 - Mon, Dec 7
PIE
St. Petersburg-Clearwater Intl.
ALB
Albany Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Dec 4 from St. Petersburg-Clearwater Intl. to Albany Intl., returning Mon, Dec 7, priced at $117 found 1 day ago
Fri, Dec 4 - Fri, Dec 11
MYR
Myrtle Beach Intl.
BDL
Bradley Intl.
$122 Roundtrip, found 1 hour ago
$122
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Dec 4 from Myrtle Beach Intl. to Bradley Intl., returning Fri, Dec 11, priced at $122 found 1 hour ago
Fri, Dec 4 - Mon, Dec 7
PIE
St. Petersburg-Clearwater Intl.
ALB
Albany Intl.
$126 Roundtrip, found 5 days ago
$126
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Fri, Dec 4 from St. Petersburg-Clearwater Intl. to Albany Intl., returning Mon, Dec 7, priced at $126 found 5 days ago
Fri, Feb 12 - Mon, Feb 22
MYR
Myrtle Beach Intl.
ALB
Albany Intl.
$130 Roundtrip, found 5 hours ago
$130
Roundtrip
found 5 hours ago
Select Allegiant Air flight, departing Fri, Feb 12 from Myrtle Beach Intl. to Albany Intl., returning Mon, Feb 22, priced at $130 found 5 hours ago
Thu, Jan 7 - Sun, Jan 17
TPA
Tampa Intl.
ALB
Albany Intl.
$149 Roundtrip, found 7 hours ago
$149
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, Jan 7 from Tampa Intl. to Albany Intl., returning Sun, Jan 17, priced at $149 found 7 hours ago
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$156 Roundtrip, found 1 day ago
$156
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Bradley Intl., returning Mon, Dec 7, priced at $156 found 1 day ago
Thu, Oct 29 - Sat, Nov 7
TPA
Tampa Intl.
BDL
Bradley Intl.
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Oct 29 from Tampa Intl. to Bradley Intl., returning Sat, Nov 7, priced at $167 found 6 days ago
OriginDestinationTravel DatesFlights From*
RSWLathamJanuary 13 to January 23$152
RSWWindsor LocksDecember 8 to December 12$158
JFKWindsor LocksOctober 22 to October 25$277
JFKLathamOctober 26 to October 27$323
MANWindsor LocksNovember 10 to November 17$806
MANLathamDecember 16 to December 30$1,395
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWLathamOctober 10 to October 21$292
RSWWindsor LocksOctober 11 to October 14$323
JFKWindsor LocksOctober 10 to October 13$458
JFKLathamOctober 11 to October 15$522
*Prices include taxes and fees

Best Berkshire County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Brook Bound Inn
2.0-star property

Brook Bound Inn

Nov 19 - Nov 22

3 night stay

Houston (IAH) to Albany (ALB)

United • Non-stop roundtrip • Coach
Price was $981, price is now $772 per person
$772
per person
found 1 day ago
Aspen At Manchester
2.5-star property

Aspen At Manchester

Oct 23 - Oct 27

4 night stay

New York (JFK) to Albany (ALB)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,475, price is now $1,113 per person
$1,113
per person
found 1 day ago
Prospect Berkshires
3.0-star property

Prospect Berkshires

Oct 18 - Oct 24

6 night stay

Houston (IAH) to Albany (ALB)

American Airlines • Non-stop roundtrip • Coach
Price was $3,071, price is now $2,395 per person
$2,395
per person
found 4 hours ago
Don't see what you're looking for?
See all available trips from Houston to Berkshire County
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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.
8.8/10 Excellent! (2,709 reviews)
"Recommend hotel to provide breakfast and extend checkout time to 11 am."

Reviewed on Oct 5, 2026

Opens in a new windowVacation Village in the Berkshires
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.
9/10 Wonderful! (1,174 reviews)
"Great place"

Reviewed on Oct 5, 2026

Opens in a new windowBerkshire Mountain Lodge
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
8.6/10 Excellent! (1,004 reviews)
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."

Reviewed on Oct 5, 2026

Opens in a new windowQuality Inn Great Barrington
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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! (1,007 reviews)
"Gave my jacuzzi room, that I paid extra for, away to the wrong person because we had the same first name."

Reviewed on Oct 4, 2026

Opens in a new windowThe Yankee 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 $116. 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 January. 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 $116. 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 $116 and $1,395. 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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