$49 Cheap flights to Berkshire County

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Top places to visit in Berkshire County

A town hall with a central dome and columns, surrounded by trees and people.
FlightsFlights
FlightsFlights

Lenox

Lenox

Cheap flights to Berkshire County from $49 One Way, $84 Round Trip

$84 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.

Fri, Dec 4 - Mon, Dec 7
PIE
St. Petersburg
ALB
Albany
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Fri, Dec 4 from St. Petersburg to Albany, returning Mon, Dec 7, priced at $84 found 2 days ago
Thu, Oct 29 - Sun, Nov 1
FLL
Fort Lauderdale
ALB
Albany
$98 Roundtrip, found 1 hour ago
$98
Roundtrip
found 1 hour ago
Select Allegiant Air flight, departing Thu, Oct 29 from Fort Lauderdale to Albany, returning Sun, Nov 1, priced at $98 found 1 hour ago
Sat, Sep 12 - Wed, Sep 16
RDU
Raleigh
BDL
Hartford
$112 Roundtrip, found 13 hours ago
$112
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh to Hartford, returning Wed, Sep 16, priced at $112 found 13 hours ago
Thu, Jan 14 - Sun, Jan 17
RDU
Raleigh
ALB
Albany
$122 Roundtrip, found 2 days ago
$122
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jan 14 from Raleigh to Albany, returning Sun, Jan 17, priced at $122 found 2 days ago
Tue, Oct 20 - Sat, Oct 31
TPA
Tampa
BDL
Hartford
$142 Roundtrip, found 6 days ago
$142
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Oct 20 from Tampa to Hartford, returning Sat, Oct 31, priced at $142 found 6 days ago
Tue, Aug 11 - Mon, Aug 31
MCO
Orlando
BDL
Hartford
$149 Roundtrip, found 4 days ago
$149
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Aug 11 from Orlando to Hartford, returning Mon, Aug 31, priced at $149 found 4 days ago
Wed, Aug 19 - Wed, Sep 2
FLL
Fort Lauderdale
BDL
Hartford
$158 Roundtrip, found 15 hours ago
$158
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from Fort Lauderdale to Hartford, returning Wed, Sep 2, priced at $158 found 15 hours ago
Wed, Aug 12 - Wed, Aug 26
MCO
Orlando
BDL
Hartford
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando to Hartford, returning Wed, Aug 26, priced at $177 found 1 day ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
RSWLathamJuly 25 to August 1$258
RSWWindsor LocksJuly 26 to July 30$360
JFKWindsor LocksJuly 25 to July 26$448
JFKLathamJuly 25 to August 11$570
*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
$153 nightly
The price is $171 total per night from Jul 22 to Jul 23
$171 total
Jul 22 - Jul 23
Total with taxes and fees
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 ...
8.8/10 Excellent! (2,463 reviews)
"There were some maintenance issues in my room which needed to be addressed."

Reviewed on Jul 21, 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
$161 nightly
The price is $179 total per night from Aug 16 to Aug 17
$179 total
Aug 16 - Aug 17
Total with taxes and fees
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 ...
8.8/10 Excellent! (1,003 reviews)
"This was a beautiful hotel close to the best part of North Adams. The gallery on the lobby floor gives it an upscale vibe but without too high a price tag. It was very convenient for our college visit to Williams College. It was very quiet even directly across from the elevator. The beds were very ..."

Reviewed on Jul 17, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
$118 nightly
The price is $132 total per night from Aug 10 to Aug 11
$132 total
Aug 10 - Aug 11
Total with taxes and fees
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 ...
8.6/10 Excellent! (1,005 reviews)
"Great experience. Friendly staff. Easy walk to town."

Reviewed on Jul 18, 2026

Opens in a new windowQuality Inn Great Barrington
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $189 total per night from Jul 22 to Jul 23
$189 total
Jul 22 - Jul 23
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! (1,009 reviews)
"It's a reasonable and clean hotel. The breakfast is also reasonable, especially if someone likes pork and pork sausages. But the internet is absolutely not working because it's extremely weak, about 1-5 MB/s and it's not reliable, especially on the 2nd floor. It's just impossible to use internet ..."

Reviewed on Jul 21, 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.

Need a Car For After Your Flight?

Standard

Volkswagen Jetta
  • 5 people
  • Unlimited mileage
Albany, New York, USA
Volkswagen Jetta

$177

$472 total
found 2 days ago
Standard Volkswagen Jetta

Fullsize

Toyota Camry
  • 5 people
  • Unlimited mileage
Albany, New York, USA
Toyota Camry

$178

$475 total
found 2 days ago
Fullsize Toyota Camry

Midsize SUV

Mazda CX-50
  • 5 people
  • Unlimited mileage
Albany, New York, USA
Mazda CX-50

$183

$488 total
found 2 days ago
Midsize SUV Mazda CX-50
Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.

Berkshire County

Orbitz uses cutting edge mobile technology to help get you the best deals on Berkshire County flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Berkshire County Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Berkshire County, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Berkshire County can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Berkshire County. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Berkshire County to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

Frequently asked questions

Which airlines fly to Berkshire County?
Check your passport is up to date and choose from the 16 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 $84 to $570 this last week. The cheapest one-way ticket prices were $49, originating in Fort Lauderdale (FLL).
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.