$48 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 $48 One Way, $102 Round Trip

$102 return flights and $48 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.

Mon, Aug 24 - Fri, Aug 28
RDU
Raleigh
ALB
Albany
$102 Roundtrip, found 6 hours ago
$102
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Mon, Aug 24 from Raleigh to Albany, returning Fri, Aug 28, priced at $102 found 6 hours ago
Sat, Aug 29 - Sat, Sep 5
RDU
Raleigh
BDL
Hartford
$112 Roundtrip, found 1 hour ago
$112
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Aug 29 from Raleigh to Hartford, returning Sat, Sep 5, priced at $112 found 1 hour ago
Fri, Jun 5 - Wed, Jun 10
MCO
Orlando
BDL
Hartford
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jun 5 from Orlando to Hartford, returning Wed, Jun 10, priced at $137 found 4 days ago
Thu, Aug 27 - Mon, Aug 31
TPA
Tampa
BDL
Hartford
$149 Roundtrip, found 9 hours ago
$149
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Aug 27 from Tampa to Hartford, returning Mon, Aug 31, priced at $149 found 9 hours ago
Sat, Jun 6 - Wed, Jun 10
MCO
Orlando
BDL
Hartford
$153 Roundtrip, found 2 days ago
$153
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Orlando to Hartford, returning Wed, Jun 10, priced at $153 found 2 days ago
Fri, Sep 4 - Mon, Sep 7
FLL
Fort Lauderdale
BDL
Hartford
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Sep 4 from Fort Lauderdale to Hartford, returning Mon, Sep 7, priced at $181 found 2 days ago
Mon, Aug 17 - Wed, Aug 26
FLL
Fort Lauderdale
ALB
Albany
$187 Roundtrip, found 4 days ago
$187
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Aug 17 from Fort Lauderdale to Albany, returning Wed, Aug 26, priced at $187 found 4 days ago
Tue, Aug 11 - Wed, Aug 12
RDU
Raleigh
BDL
Hartford
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 11 from Raleigh to Hartford, returning Wed, Aug 12, priced at $192 found 1 day ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
RSWWindsor LocksMay 30 to June 7$220
JFKWindsor LocksMay 29 to May 30$417
RSWLathamMay 31 to June 6$556
JFKLathamMay 30 to May 31$723
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Berkshire County Accommodation Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from May 26 to May 27
$126 total
May 26 - May 27
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! (948 reviews)
"Everything great"

Reviewed on May 24, 2026

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from May 26 to May 27
$133 total
May 26 - May 27
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! (959 reviews)
"Great location, clean and spacious room, lobby area was very relaxing! We enjoyed the coffee available at the front as well."

Reviewed on May 24, 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
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from May 26 to May 27
$123 total
May 26 - May 27
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! (2,368 reviews)
"Place is showing its age walls are thin Have to use the car to get to the pool No alarm clock or anywhere that had a usb charger port"

Reviewed on May 25, 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
Fully refundable
$152 nightly
The price is $170 total per night from Jun 1 to Jun 2
$170 total
Jun 1 - Jun 2
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! (1,003 reviews)
"I loved the use of space for local artists to display there art. Beautiful work. The hotel was very clean. Loved that you could get a coffee or water throughout the day. I wish that the pool was opened all day. Ample parking"

Reviewed on May 23, 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.

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

Orbitz provides convenient, one-stop shopping for travelers looking for budget flights to Berkshire County or any other low fare domestic or international air travel.

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Stay on Budget, Earn Miles with Bargain Berkshire County Flights

You can find amazing discount fares with Orbitz’s guaranteed low prices or take advantage of last-minute sales and special travel packages. You can also earn points towards your airline frequent flyer programs when you book qualified flights to Berkshire County. That means you can rack up money-saving points and miles for future use while saving money now.

We Are Just a Phone Call Away If You Need Us

Booking, changing, or canceling your Berkshire County flights is a breeze with Orbitz’s online and mobile tools, but that doesn't mean that we leave you hanging if you want to speak with one of our representatives. If you need help, just contact our Customer Service by email or phone. To enjoy a less stressful trip, be sure to sign up for instant alerts so we can send you any updates or delays relating to your flights to Berkshire County to your mobile phone or email.

Frequently asked questions

Which airlines fly to Berkshire County?
Check your passport is up to date and choose from the 15 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 $102 to $723 this last week. The cheapest one-way ticket prices were $48, 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.