Cheap Flights to Berkshire County (2026/2027)

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Lenox

Flights
Lenox
OriginDestinationTravel DatesFlights From*
RSWLathamSeptember 5 to September 12$112
RSWWindsor LocksAugust 29 to September 6$152
JFKWindsor LocksJune 13 to June 15$247
JFKLathamJuly 11 to July 17$309
MANWindsor LocksJuly 14 to August 10$1,146
MANLathamJuly 13 to July 20$1,194
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWLathamJune 6 to June 13$138
JFKWindsor LocksJune 5 to June 7$202
RSWWindsor LocksJune 6 to June 9$213
JFKLathamJune 5 to June 10$512
*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

Jul 10 - Jul 14

4 night stay

Boston (BOS) to Albany (ALB)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,295, price is now $901 per person
$901
per person
found 18 hours ago
Lodges At Cresthaven
4.0-star property

Lodges At Cresthaven

Jul 10 - Jul 14

4 night stay

Boston (BOS) to Albany (ALB)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,449, price is now $1,664 per person
$1,664
per person
found 18 hours ago
Hilton Garden Inn Saratoga Springs
3.0-star property

Hilton Garden Inn Saratoga Springs

Jul 10 - Jul 14

4 night stay

Boston (BOS) to Albany (ALB)

Delta • Non-stop roundtrip • Coach
Price was $1,297, price is now $966 per person
$966
per person
found 18 hours ago
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Travelers ❤️ These Berkshire County 🏨

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! (959 reviews)
"Hot tub doesn’t go above 95 which is colder than you think, didn’t have any luggage carts available after asking 3 different people, but it’s a charming place to end on a positive note"

Reviewed on May 28, 2026

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
9/10 Wonderful! (962 reviews)
"The converted motel has several appealing features — it was clean, the Le Labo products smelled wonderful, and the lobby bar is beautifully designed. Unfortunately, the level of service fell well below expectations. Two days before our arrival, I received a survey asking whether we’d like any additional ..."

Reviewed on May 27, 2026

Opens in a new windowBerkshires Untold
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! (2,378 reviews)
"Beautiful property in the middle of the mountains"

Reviewed on May 28, 2026

Opens in a new windowVacation Village in the Berkshires
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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 breakfast, free WiFi, and free parking. 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! (1,000 reviews)
"Room was newly completed and fresh."

Reviewed on May 25, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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 $112. 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 6 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 September. 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 $112. 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 $112 and $1,194. 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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