$46 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 $46 One Way, $88 Round Trip

$88 return flights and $46 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, Aug 30 - Fri, Sep 5
MCO
Orlando
BDL
Hartford
$88 Roundtrip, found 1 hour ago
$88
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Aug 30 from Orlando to Hartford, returning Fri, Sep 5, priced at $88 found 1 hour ago
Sat, Aug 30 - Fri, Sep 5
MCO
Orlando
BDL
Hartford
$89 Roundtrip, found 1 hour ago
$89
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando to Hartford, returning Fri, Sep 5, priced at $89 found 1 hour ago
Sat, Sep 20 - Sun, Sep 21
CHS
Charleston
BDL
Hartford
$92 Roundtrip, found 3 days ago
$92
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Sep 20 from Charleston to Hartford, returning Sun, Sep 21, priced at $92 found 3 days ago
Thu, Aug 28 - Sun, Aug 31
MCO
Orlando
BDL
Hartford
$101 Roundtrip, just found
$101
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Aug 28 from Orlando to Hartford, returning Sun, Aug 31, priced at $101 just found
Wed, Sep 24 - Sat, Sep 27
CHS
Charleston
ALB
Albany
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Sep 24 from Charleston to Albany, returning Sat, Sep 27, priced at $102 found 2 days ago
Thu, Sep 4 - Thu, Sep 11
MCO
Orlando
ALB
Albany
$112 Roundtrip, found 2 days ago
$112
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando to Albany, returning Thu, Sep 11, priced at $112 found 2 days ago
Fri, Sep 5 - Mon, Sep 8
RDU
Raleigh
BDL
Hartford
$116 Roundtrip, found 2 days ago
$116
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Raleigh to Hartford, returning Mon, Sep 8, priced at $116 found 2 days ago
Fri, Dec 5 - Mon, Dec 15
TPA
Tampa
BDL
Hartford
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 5 from Tampa to Hartford, returning Mon, Dec 15, priced at $122 found 1 day ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
RSWWindsor LocksJuly 27 to August 13$202
JFKWindsor LocksJuly 27 to August 8$258
JFKLathamJuly 26 to August 6$581
RSWLathamJuly 26 to July 29$781
*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
$120 nightly
The price is $134 total per night from Aug 4 to Aug 5
$134 total
Aug 4 - Aug 5
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! (1,890 reviews)
"I loved the mountains all around, beautiful scenery."

Reviewed on Jul 21, 2025

Vacation Village in the Berkshires
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
$170 nightly
The price is $190 total per night from Jul 27 to Jul 28
$190 total
Jul 27 - Jul 28
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! (1,004 reviews)
"Great place"

Reviewed on Jul 16, 2025

Hotel Downstreet, Ascend Hotel Collection
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
$269 nightly
The price is $301 total per night from Aug 10 to Aug 11
$301 total
Aug 10 - Aug 11
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! (473 reviews)
"We did not care for the barn door to the bathroom. Wouldn't stay closed and large gap meant a loud radio or TV required... Otherwise, our stay was great and we would definitely recommend it."

Reviewed on Jul 22, 2025

The Williams Inn
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Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
$129 nightly
The price is $144 total per night from Jul 27 to Jul 28
$144 total
Jul 27 - Jul 28
Total includes taxes and fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (829 reviews)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield."

Reviewed on Jul 21, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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

Orbitz uses cutting edge mobile technology to help get you the best deals on Berkshire County flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Berkshire County Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Berkshire County, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Berkshire County can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Berkshire County. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Berkshire County to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

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 $88 to $781 this last week. The cheapest one-way ticket prices were $46, originating in Charleston (CHS).
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

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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.