$42 Cheap flights to Berkshire County

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Top places to visit in Berkshire County

Lenox which includes an administrative buidling
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Lenox

Lenox

Cheap flights to Berkshire County from $42 One Way, $93 Round Trip

$93 return flights and $42 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.

Sat, Jul 26 - Mon, Jul 28
FLL
Fort Lauderdale
BDL
Hartford
$93 Roundtrip, found 2 hours ago
$93
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Jul 26 from Fort Lauderdale to Hartford, returning Mon, Jul 28, priced at $93 found 2 hours ago
Fri, Sep 12 - Mon, Sep 15
RDU
Raleigh
ALB
Albany
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Fri, Sep 12 from Raleigh to Albany, returning Mon, Sep 15, priced at $98 found 3 days ago
Fri, Aug 29 - Sun, Aug 31
MCO
Orlando
BDL
Hartford
$102 Roundtrip, found 3 days ago
$102
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Aug 29 from Orlando to Hartford, returning Sun, Aug 31, priced at $102 found 3 days ago
Sat, Aug 2 - Mon, Aug 18
MCO
Orlando
BDL
Hartford
$110 Roundtrip, found 3 days ago
$110
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Aug 2 from Orlando to Hartford, returning Mon, Aug 18, priced at $110 found 3 days ago
Fri, Sep 5 - Mon, Sep 8
RDU
Raleigh
BDL
Hartford
$121 Roundtrip, found 3 hours ago
$121
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Sep 5 from Raleigh to Hartford, returning Mon, Sep 8, priced at $121 found 3 hours ago
Thu, Sep 4 - Thu, Sep 11
MCO
Orlando
ALB
Albany
$132 Roundtrip, found 11 hours ago
$132
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando to Albany, returning Thu, Sep 11, priced at $132 found 11 hours ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
RSWWindsor LocksJuly 12 to July 14$187
JFKWindsor LocksJuly 12 to July 23$239
RSWLathamJuly 13 to July 17$322
JFKLathamJuly 12 to July 29$493
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Berkshire County Accommodation Deals

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $160 total per night from Aug 4 to Aug 5
$160 total
Aug 4 - Aug 5
Total includes taxes and fees
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,001 reviews)
"Fantastic place"

Reviewed on Jul 2, 2025

Hotel Downstreet, Ascend Hotel Collection
Prospect Berkshires

Prospect Berkshires

2 out of 5
50 Prospect Lake Rd, Egremont, MA
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Catamount Aerial Adventure Park and Catamount ...
Get rates
Prospect Berkshires
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
$117 nightly
The price is $131 total per night from Jul 7 to Jul 8
$131 total
Jul 7 - Jul 8
Total includes taxes and fees
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,847 reviews)
"amazing for the price and overall SOOO clean"

Reviewed on Jun 28, 2025

Vacation Village in the Berkshires
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The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
$247 nightly
The price is $276 total per night from Jul 9 to Jul 10
$276 total
Jul 9 - Jul 10
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (459 reviews)
"Wonderful stay. Helpful, professional staff."

Reviewed on Jun 27, 2025

The Williams 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?

Midsize SUV

Jeep Compass or similar
  • 5 people
  • Unlimited mileage
Albany, New York, USA
Jeep Compass

$56

$149 total
found 2 days ago
Midsize SUV Jeep Compass

Compact SUV

Hyundai Kona or similar
  • 5 people
  • Unlimited mileage
Albany, New York, USA
Hyundai Kona

$60

$161 total
found 2 days ago
Compact SUV Hyundai Kona

Standard Recreational Vehicle

Jeep Wrangler 4-Door or similar
  • 4 people
  • Unlimited mileage
Albany, New York, USA
Jeep Wrangler 4-Door

$65

$173 total
found 2 days ago
Standard Recreational Vehicle Jeep Wrangler 4-Door

Premium Pickup Regular Cab

Ford F150 or similar
  • 5 people
  • Unlimited mileage
Albany, New York, USA
Ford F150

$71

$190 total
found 2 days ago
Premium Pickup Regular Cab Ford F150
Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.

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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Now it is even faster to find exclusive deals and book cheap Berkshire County flights from any location with our new Orbitz apps. These cutting-edge mobile tools are available free to anyone with an Android device, iPad, or iPhone. Look up Berkshire County's most popular attractions, best restaurants, and entertainment venues or check on your flights to Berkshire County and make changes to your itinerary while waiting in line for your latte.

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 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 $93 to $493 this last week. The cheapest one-way ticket prices were $42, 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.

City Destinations in Berkshire County

Airlines Operating

Book on Expedia

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.