$38 Cheap flights to Berkshire County

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Top places to visit in Berkshire County

Williamstown featuring cafe lifestyle
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Williamstown

Williamstown

Cheap flights to Berkshire County from $38 One Way, $81 Round Trip

$81 return flights and $38 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, Aug 28 - Sun, Aug 31
MCO
Orlando
BDL
Hartford
$81 Roundtrip, just found
$81
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Aug 28 from Orlando to Hartford, returning Sun, Aug 31, priced at $81 just found
Thu, Sep 4 - Mon, Sep 8
MCO
Orlando
BDL
Hartford
$81 Roundtrip, found 17 hours ago
$81
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando to Hartford, returning Mon, Sep 8, priced at $81 found 17 hours ago
Sat, Aug 23 - Mon, Aug 25
FLL
Fort Lauderdale
BDL
Hartford
$94 Roundtrip, found 4 days ago
$94
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Aug 23 from Fort Lauderdale to Hartford, returning Mon, Aug 25, priced at $94 found 4 days ago
Thu, Aug 21 - Sun, Aug 24
MCO
Orlando
BDL
Hartford
$97 Roundtrip, found 15 hours ago
$97
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Thu, Aug 21 from Orlando to Hartford, returning Sun, Aug 24, priced at $97 found 15 hours ago
Sun, Sep 14 - Thu, Sep 18
RDU
Raleigh
ALB
Albany
$99 Roundtrip, found 2 days ago
$99
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Sep 14 from Raleigh to Albany, returning Thu, Sep 18, priced at $99 found 2 days ago
Thu, Sep 4 - Tue, Sep 23
LAX
Los Angeles
BDL
Hartford
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 4 from Los Angeles to Hartford, returning Tue, Sep 23, priced at $100 found 3 days ago
Sat, Sep 6 - Sat, Sep 13
TPA
Tampa
BDL
Hartford
$101 Roundtrip, found 14 hours ago
$101
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Sat, Sep 6 from Tampa to Hartford, returning Sat, Sep 13, priced at $101 found 14 hours ago
Mon, Sep 29 - Wed, Oct 1
RDU
Raleigh
BDL
Hartford
$116 Roundtrip, found 3 days ago
$116
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Sep 29 from Raleigh to Hartford, returning Wed, Oct 1, priced at $116 found 3 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
RSWWindsor LocksAugust 15 to August 18$153
JFKWindsor LocksAugust 15 to August 22$206
RSWLathamAugust 17 to August 28$365
JFKLathamAugust 15 to August 17$910
*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
$130 nightly
The price is $145 total per night from Aug 27 to Aug 28
$145 total
Aug 27 - Aug 28
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! (1,931 reviews)
"Studio was nice and spacious. I got there late and left early so didn’t take advantage of amenities but they looked nice."

Reviewed on Aug 5, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $145 total per night from Sep 7 to Sep 8
$145 total
Sep 7 - Sep 8
Total includes taxes and fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (543 reviews)
"Very spacious room with full kitchen. Definitely worth the price. Would use again"

Reviewed on Aug 5, 2025

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $88 total per night from Aug 10 to Aug 11
$88 total
Aug 10 - Aug 11
Total includes taxes and fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (763 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on Aug 2, 2025

FairBridge Inn Express
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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
$233 nightly
The price is $260 total per night from Sep 7 to Sep 8
$260 total
Sep 7 - Sep 8
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! (482 reviews)
"The property was spacious but still had a cozy feel."

Reviewed on Jul 29, 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?

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 discount prices on flights to Berkshire County then look no further than Orbitz. With some of the best deals available, cutting-edge technology, and great customer service, Orbitz makes booking Berkshire County flights easy and affordable.

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By using Orbitz’s free apps for iPhone and Android, and an easy-to-use mobile browser at m.orbitz.com, booking flights to Berkshire County has never been so convenient. Check for updates and alerts wherever you are, or manage your booking quickly. And we also offer mobile exclusive deals on hotels, so don’t delay—book right away.

The Complete Package

Orbitz makes it stress-free to book Berkshire County flights, and we can also help you figure out the rest of your trip just as easily. If you need great deals on hotels and car rentals following your flights to Berkshire County, just add the details to your booking and search for the cheapest deals out there. And why waste time lining up for admission to attractions and events? With Orbitz, you can book tickets in advance and waltz straight in.

Low Price Guarantee

Booking your Berkshire County flights with Orbitz guarantees low prices every day, all day—no matter when and where you book. You will always find the best deals available, coupled with extra great savings and discounts for all around great value.

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 $81 to $910 this last week. The cheapest one-way ticket prices were $38, 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.