$49 Cheap flights to Berkshire County

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Top places to visit in Berkshire County

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Lenox

Lenox

Cheap flights to Berkshire County from $49 One Way, $90 Round Trip

$90 return flights and $49 one-way flights to Berkshire County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Nov 5 - Thu, Nov 12
SFB
Orlando
ALB
Albany
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Nov 5 from Orlando to Albany, returning Thu, Nov 12, priced at $90 found 1 day ago
Thu, Oct 1 - Sun, Oct 4
FLL
Fort Lauderdale
ALB
Albany
$98 Roundtrip, found 23 hours ago
$98
Roundtrip
found 23 hours ago
Select Allegiant Air flight, departing Thu, Oct 1 from Fort Lauderdale to Albany, returning Sun, Oct 4, priced at $98 found 23 hours ago
Fri, Dec 4 - Mon, Dec 7
PIE
St. Petersburg
ALB
Albany
$108 Roundtrip, found 6 days ago
$108
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Dec 4 from St. Petersburg to Albany, returning Mon, Dec 7, priced at $108 found 6 days ago
Sat, Sep 26 - Mon, Sep 28
MCO
Orlando
BDL
Hartford
$144 Roundtrip, found 2 hours ago
$144
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Orlando to Hartford, returning Mon, Sep 28, priced at $144 found 2 hours ago
Fri, Oct 2 - Mon, Oct 5
MCO
Orlando
BDL
Hartford
$146 Roundtrip, found 3 days ago
$146
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Oct 2 from Orlando to Hartford, returning Mon, Oct 5, priced at $146 found 3 days ago
Thu, Oct 29 - Wed, Nov 4
TPA
Tampa
BDL
Hartford
$147 Roundtrip, found 7 hours ago
$147
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, Oct 29 from Tampa to Hartford, returning Wed, Nov 4, priced at $147 found 7 hours ago
Sat, Sep 26 - Mon, Sep 28
MCO
Orlando
BDL
Hartford
$153 Roundtrip, found 2 hours ago
$153
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Orlando to Hartford, returning Mon, Sep 28, priced at $153 found 2 hours ago
Fri, Nov 13 - Mon, Nov 16
FLL
Fort Lauderdale
BDL
Hartford
$158 Roundtrip, found 21 hours ago
$158
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Fri, Nov 13 from Fort Lauderdale to Hartford, returning Mon, Nov 16, priced at $158 found 21 hours ago
Thu, Jan 21 - Thu, Jan 28
TPA
Tampa
ALB
Albany
$176 Roundtrip, found 4 days ago
$176
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jan 21 from Tampa to Albany, returning Thu, Jan 28, priced at $176 found 4 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
RSWWindsor LocksAugust 29 to September 5$288
JFKWindsor LocksAugust 28 to September 25$377
RSWLathamAugust 29 to August 30$506
JFKLathamAugust 29 to August 30$679
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Berkshire County Accommodation Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $143 total per night from Aug 31 to Sep 1
$143 total
Aug 31 - Sep 1
Total with taxes and fees
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 ...
8.8/10 Excellent! (2,556 reviews)
"Price - quality =awesome"

Reviewed on Aug 22, 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
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $176 total per night from Sep 14 to Sep 15
$176 total
Sep 14 - Sep 15
Total with taxes and fees
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 ...
9.2/10 Wonderful! (1,018 reviews)
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."

Reviewed on Aug 22, 2026

Opens in a new windowThe Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $139 total per night from Aug 31 to Sep 1
$139 total
Aug 31 - Sep 1
Total with taxes and fees
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 ...
9/10 Wonderful! (1,087 reviews)
"A convenient place to stay for Tanglewood events. Fully equipped kitchen, free laundry room and quiet. Sofa is uncomfortable."

Reviewed on Aug 23, 2026

Opens in a new windowBerkshire Mountain Lodge
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FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
$61 nightly
The price is $68 total per night from Aug 24 to Aug 25
$68 total
Aug 24 - Aug 25
Total with taxes and fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
Opens in a new windowFairBridge Inn Express
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Berkshire County

Traveling to Berkshire County and need a cheap flight? Orbitz has great deals on flights to Berkshire County right now. Plus, we offer big discounts on hotel rooms and car rentals for a great money-saving trip.

Find Low Cost Flights to Berkshire County Quickly and Hassle-Free

There are many Internet sites that promise cheap Berkshire County flights, but a busy, bargain-minded trip planner needs more than just budget air tickets. Not only does Orbitz offer the best deals for domestic and international air fare, but we also provide the resources and tools to help you plan your flights to Berkshire County, book your lodging, and look up key attractions in Berkshire County. Our easy search tools and guaranteed low prices let you budget your time and your money so you have more of both to spend on your vacation.

New Apps Make Booking Berkshire County Flights Easier Than Ever

You no longer need to be sitting at your computer to find amazing Orbitz sales for flights to Berkshire County now we offer cutting-edge mobile tools for many Android and iOS gadgets. These free apps allow you to run a search for discount air fare, look for special vacation packages, or check on your booked Berkshire County flights from any location. Some special deals are only available for mobile customers, so be sure to take advantage of these free downloads today.

Orbitz Customers Are Truly #1

Orbitz takes pride in providing the best customer experience possible, and that effort doesn't end with discount flights to Berkshire County or user-friendly mobile apps and web tools. Orbitz Customer Service is always ready to answer questions and help you with booking, planning, or canceling your Berkshire County flights. When you need us, we’re here for you!

Frequently asked questions

Which airlines fly to Berkshire County?
Check your passport is up to date and choose from the 18 airlines that fly to Bradley Intl. Airport (BDL). Once you've left the plane, Berkshire County is yours to discover. Find amazing deals from these leading carriers:

  • Air Canada - 17 flights to Berkshire County per month
  • JetBlue - 16 flights to Berkshire County per month

How much is a flight to Berkshire County?
If you're hunting down round-trip flights, airfares ranged from $90 to $679 this last week. The cheapest one-way ticket prices were $49, originating in Orlando (SFB).
How to book the cheapest flight to Berkshire County?
With some of the most incredible flight deals around, you can jet for less with Orbitz. The following pointers will help you find cheap flights to Berkshire County — and leave you with more money to play with:

  • Taking off from or arriving at nearby airports may help you save on airfares. Enter your preferred departure and arrival points. Next, select the 'Nearby airports' function below the form fields to compare your options.
  • If your plans aren't written in stone, click on the 'Show flexible dates' link to check out the flight deals for different departure dates. You may find an amazing fare.
  • You can also use the 'Show options' function to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you want to fly.
  • Lock in your fare as soon as you've decided on your travel dates. While you can get lucky once in a while, tickets rarely drop in price as your date of departure approaches.
  • Save loads on your trip by combining your hotel, flights and car rental into an Orbitz package. Your credit card will thank you for it.
  • Don't fly during peak seasons if possible. By avoiding school vacations and summer, you can save big on your airfares.

What is the best time to book a flight to Berkshire County?
Generally speaking, January is the best month to book your airfare. This is followed by February and August. Keep this in mind while tracking down a cheap flight to Berkshire County.
What day of the week is the cheapest to book a flight to Berkshire County?
To land a rewarding flight deal, make a booking on a Tuesday, Wednesday or Saturday. These are usually the cheapest days to purchase flights to Berkshire County.
What is the cheapest day of the week to fly to Berkshire County?
Consider departing early in the week if you want to get cheap flights to Berkshire County. Orbitz data from 2020 indicates Monday is generally the cheapest day to start your trip, followed by Tuesday. Saturdays were shown to have the most expensive ticket fares. Presumably, this is because many travelers prefer to kick off their break on a weekend.
What is the cheapest month to fly to Berkshire County?
Get set to jet for less in August. This is generally an excellent month to get on a plane if you're looking for cheap flights to Berkshire County, according to Orbitz data. The most expensive time to take off is June, so avoid this month if possible.
Which airlines allow free cancellation?
Orbitz makes it a snap to find carriers offering fare flexibility. Simply choose "Filter by flexible change policies" when searching for your flights and bada bing, bada boom! You'll see options that include free cancellation within 24 hours of booking, no change fees and of course, an irresistible low price.
What do I need for the flight to Berkshire County?
Whether you're familiar with flying or it's your first time on a plane, it's always great to be organized on your journey. Here are a few things to bear in mind:

  • Travel paperwork such as e-tickets and identification are a must. To avoid any delays when you check in, make sure your booking is made with the exact name, birth date and gender as indicated on your government-issued ID.
  • A well-packed carry-on bag is just the ticket for a great flight experience. Given this journey to Berkshire County is no short hop, take a few snacks and things to keep you happy. Something to read or listen to is sure to help pass the time.
  • Air conditioning and high altitudes can form a cool environment. No matter what the season is in Berkshire County, carry a sweater with you to keep nice and warm while on the plane.

How do I get cheap first-class/business deals to Berkshire County?
Savvy travelers are pros at finding business or first-class fares to Berkshire County that don't cost an arm and a leg. You can do the same with these helpful tips:

  • Flexibility is everything. By being open to other travel dates, you'll have a better chance of picking up a great deal on business or first-class airfares.
  • Look for a budget carrier that has seats in business class. They often come with more legroom and a glass of Champagne — and a nicer price.
  • Make a bid for an upgrade. Some airlines hold online auctions that let you put down a price for a seat at the front of the plane. You may also be able to upgrade with points earned through a flight loyalty program.

What is the best time to go to Berkshire County?
If you want to soak up the vibe of Berkshire County in the peak season, February, March and May are the best months to visit. June 20 marks the beginning of summer in the Northern Hemisphere and is a perfect time to go if you enjoy the open air. At this time of year, average daily temperatures usually range from 55 ºF to 75 ºF.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.