$55 Cheap flights to Berkshire County

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Top places to visit in Berkshire County

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

Lenox

Cheap flights to Berkshire County from $55 One Way, $98 Round Trip

$98 return flights and $55 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, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale
ALB
Albany
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Allegiant Air flight, departing Thu, Sep 3 from Fort Lauderdale to Albany, returning Sun, Sep 6, priced at $98 just found
Mon, Aug 31 - Mon, Aug 31
MCO
Orlando
BDL
Hartford
$111 Roundtrip, found 2 hours ago
$111
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Orlando to Hartford, returning Mon, Aug 31, priced at $111 found 2 hours ago
Thu, Sep 10 - Mon, Sep 21
MCO
Orlando
BDL
Hartford
$133 Roundtrip, found 1 hour ago
$133
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando to Hartford, returning Mon, Sep 21, priced at $133 found 1 hour ago
Thu, Oct 1 - Mon, Oct 5
FLL
Fort Lauderdale
ALB
Albany
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 1 from Fort Lauderdale to Albany, returning Mon, Oct 5, priced at $159 found 1 day ago
Fri, Aug 14 - Wed, Aug 19
FLL
Fort Lauderdale
BDL
Hartford
$174 Roundtrip, found 6 days ago
$174
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Aug 14 from Fort Lauderdale to Hartford, returning Wed, Aug 19, priced at $174 found 6 days ago
Mon, Sep 21 - Mon, Sep 28
MCO
Orlando
ALB
Albany
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 21 from Orlando to Albany, returning Mon, Sep 28, priced at $188 found 1 day ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
JFKWindsor LocksJuly 12 to July 26$329
RSWWindsor LocksJuly 12 to July 18$399
RSWLathamJuly 12 to July 19$741
JFKLathamJuly 12 to July 13$1,269
MANWindsor LocksJuly 12 to July 16$1,350
*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
$143 nightly
The price is $159 total per night from Jul 12 to Jul 13
$159 total
Jul 12 - Jul 13
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! (2,429 reviews)
"We absolutely love it there! Colleen at the front desk has been there a very long time she's sweet as can be! everyone is so nice and helpful, and the place is relaxing and clean we stay there quite often!"

Reviewed on Jul 9, 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
$151 nightly
The price is $169 total per night from Jul 12 to Jul 13
$169 total
Jul 12 - Jul 13
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)
"The hotel is a few minutes from Tanglewood and the Berkshire hotspots. Super friendly staff. Very accommodating. The place is a bit dated, but that has a retro charm like places on the Cape. The grounds are lovely. The breakfast is like other hotel breakfast. Lots of options: cereal, oatmeal, eggs, ..."

Reviewed on Jul 9, 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
$155 nightly
The price is $173 total per night from Aug 9 to Aug 10
$173 total
Aug 9 - Aug 10
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! (1,026 reviews)
"Nice property good coffee"

Reviewed on Jul 6, 2026

Opens in a new windowBerkshire Mountain Lodge
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The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $237 total per night from Jul 22 to Jul 23
$237 total
Jul 22 - Jul 23
Total with taxes and fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,009 reviews)
"Had a lovely 2 night stay at the Red Lion Inn. The front desk staff were very welcoming. The location was convenient to many nice shops and restaurants, as well as sites like the Norman Rockwell museum and the Divine Mercies chapel and grounds. This hotel is a wonderful blend of historic and modern..and ..."

Reviewed on Jul 7, 2026

Opens in a new windowThe Red Lion 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?

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

Reach your destination without breaking your budget by booking your flights to Berkshire County using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Berkshire County Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Berkshire County flights. Using our free mobile phone apps will make you privy to a number of discounts that are unique to mobile phone users. These are perfect for harried travelers who want to find deals that they can qualify for on the same day.

Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Berkshire County. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Berkshire County, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Berkshire County flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

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Frequently asked questions

Which airlines fly to Berkshire County?
Check your passport is up to date and choose from the 12 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 $98 to $1,350 this last week. The cheapest one-way ticket prices were $55, originating in Orlando (MCO).
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.