$53 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 $53 One Way, $88 Round Trip

$88 return flights and $53 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, May 29 - Mon, Jun 8
MCO
Orlando
BDL
Hartford
$88 Roundtrip, found 5 days ago
$88
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, May 29 from Orlando to Hartford, returning Mon, Jun 8, priced at $88 found 5 days ago
Fri, Aug 21 - Mon, Aug 24
RDU
Raleigh
ALB
Albany
$97 Roundtrip, found 5 days ago
$97
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Aug 21 from Raleigh to Albany, returning Mon, Aug 24, priced at $97 found 5 days ago
Fri, Aug 28 - Sat, Sep 5
RDU
Raleigh
BDL
Hartford
$112 Roundtrip, found 12 hours ago
$112
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Fri, Aug 28 from Raleigh to Hartford, returning Sat, Sep 5, priced at $112 found 12 hours ago
Fri, May 8 - Mon, May 11
MCO
Orlando
BDL
Hartford
$121 Roundtrip, found 4 days ago
$121
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, May 8 from Orlando to Hartford, returning Mon, May 11, priced at $121 found 4 days ago
Sat, May 16 - Sun, May 17
SJU
San Juan
BDL
Hartford
$128 Roundtrip, found 12 hours ago
$128
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sat, May 16 from San Juan to Hartford, returning Sun, May 17, priced at $128 found 12 hours ago
Wed, Aug 26 - Wed, Sep 2
TPA
Tampa
BDL
Hartford
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Tampa to Hartford, returning Wed, Sep 2, priced at $142 found 3 days ago
Thu, Apr 30 - Tue, May 5
MCO
Orlando
ALB
Albany
$161 Roundtrip, found 8 hours ago
$161
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Thu, Apr 30 from Orlando to Albany, returning Tue, May 5, priced at $161 found 8 hours ago
Wed, Aug 26 - Wed, Sep 2
FLL
Fort Lauderdale
BDL
Hartford
$162 Roundtrip, found 5 days ago
$162
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Fort Lauderdale to Hartford, returning Wed, Sep 2, priced at $162 found 5 days ago
Mon, May 4 - Sat, May 9
DFW
Dallas
BDL
Hartford
$185 Roundtrip, found 1 day ago
$185
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 4 from Dallas to Hartford, returning Sat, May 9, priced at $185 found 1 day ago
Tue, May 5 - Thu, May 7
MCO
Orlando
BDL
Hartford
$217 Roundtrip, found 5 days ago
$217
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, May 5 from Orlando to Hartford, returning Thu, May 7, priced at $217 found 5 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
JFKWindsor LocksApril 25 to May 2$333
RSWWindsor LocksApril 26 to May 1$449
RSWLathamApril 26 to April 28$467
JFKLathamApril 25 to April 26$996
*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
$110 nightly
The price is $123 total per night from Apr 19 to Apr 20
$123 total
Apr 19 - Apr 20
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! (2,334 reviews)
Very nice

Reviewed on Apr 12, 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
Fully refundable
$133 nightly
The price is $149 total per night from May 14 to May 15
$149 total
May 14 - May 15
Total with taxes and fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
8.8/10 Excellent! (1,001 reviews)
Nice staff comfy bed nice views

Reviewed on Apr 8, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from May 17 to May 18
$120 total
May 17 - May 18
Total with taxes and fees
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 ...
9/10 Wonderful! (906 reviews)
Clean, hot shower. Great pressure

Reviewed on Apr 14, 2026

Opens in a new windowBerkshire Mountain Lodge
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Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $97 total per night from Apr 21 to Apr 22
$97 total
Apr 21 - Apr 22
Total with taxes and fees
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. ...
9/10 Wonderful! (900 reviews)
It’s a nice motel with a retro vibe.

Reviewed on Apr 17, 2026

Opens in a new windowBerkshires Untold
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 or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Berkshire County

If you are looking for affordable flights to Berkshire County, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Berkshire County now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Berkshire County flights. With Orbitz, booking flights to Berkshire County is easy and the lowest prices are guaranteed.

Easy self-help service offered

Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Berkshire County flights by visiting the Orbitz site or mobile application.

Orbitz looks after you

Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Berkshire County flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

After booking your Berkshire County flights, you may access your account profile on the Orbitz site and update your frequent flyer or loyalty membership details. This information will remain on the system and will be available for you to access when you make any future bookings with Orbitz.

Frequently asked questions

Which airlines fly to Berkshire County?
Check your passport is up to date and choose from the 20 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 $88 to $996 this last week. The cheapest one-way ticket prices were $53, originating in Raleigh (RDU).
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.