$35 Cheap flights to Berkshire County

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Top places to visit in Berkshire County

Williamstown featuring cafe lifestyle
FlightsFlights
FlightsFlights

Williamstown

Williamstown

Cheap flights to Berkshire County from $35 One Way, $69 Round Trip

$69 return flights and $35 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, May 31 - Sat, Jun 7
MCO
Orlando
BDL
Hartford
$69 Roundtrip, found 4 hours ago
$69
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Orlando to Hartford, returning Sat, Jun 7, priced at $69 found 4 hours ago
Thu, Jun 5 - Mon, Jun 9
MCO
Orlando
BDL
Hartford
$81 Roundtrip, found 1 day ago
$81
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando to Hartford, returning Mon, Jun 9, priced at $81 found 1 day ago
Thu, Aug 28 - Wed, Sep 3
RDU
Raleigh
BDL
Hartford
$92 Roundtrip, found 5 days ago
$92
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Aug 28 from Raleigh to Hartford, returning Wed, Sep 3, priced at $92 found 5 days ago
Thu, Jun 5 - Thu, Jun 5
FLL
Fort Lauderdale
BDL
Hartford
$98 Roundtrip, found 10 hours ago
$98
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Thu, Jun 5 from Fort Lauderdale to Hartford, returning Thu, Jun 5, priced at $98 found 10 hours ago
Fri, May 30 - Mon, Jun 2
RDU
Raleigh
ALB
Albany
$100 Roundtrip, found 2 hours ago
$100
Roundtrip
found 2 hours ago
Select Avelo Airlines flight, departing Fri, May 30 from Raleigh to Albany, returning Mon, Jun 2, priced at $100 found 2 hours ago
Tue, May 20 - Tue, May 27
MCO
Orlando
BDL
Hartford
$131 Roundtrip, found 20 hours ago
$131
Roundtrip
found 20 hours ago
Select Southwest Airlines flight, departing Tue, May 20 from Orlando to Hartford, returning Tue, May 27, priced at $131 found 20 hours ago
Loading

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
RSWWindsor LocksMay 10 to May 22$204
JFKWindsor LocksMay 11 to July 20$272
MANWindsor LocksMay 11 to May 25$739
JFKLathamMay 9 to May 12$934
RSWLathamMay 10 to May 14$1,483
*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
The price is $151 per night from May 20 to May 21
$151
includes taxes & fees
$135 per night
May 20 - May 21
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! (999 reviews)
"Very nice and funky place! Clean, friendly nice staff. Have already stayed here twice and plan to stay again!❤️"

Reviewed on Apr 18, 2025

Hotel Downstreet, Ascend Hotel Collection
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $133 per night from May 13 to May 14
$133
includes taxes & fees
$119 per night
May 13 - May 14
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (577 reviews)
"The bed was very comfortable and the area was quiet! A bit pricey but we made the reservation a bit late since this time of year is very busy in that area. I will definitely go back if needed."

Reviewed on May 3, 2025

Life House Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is $113 per night from May 18 to May 19
$113
includes taxes & fees
$101 per night
May 18 - May 19
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 ...
9/10 Wonderful! (1,000 reviews)
"Outstanding. Immaculate in every way. The pool, hot tub, room, everything connected with our stay here was truly superb. The hot breakfast, with fresh fruit was an added bonus. The staff was friendly, engaging, and a pleasure. All motels/hotels should be like this. Simply a wonderful experience."

Reviewed on May 5, 2025

The Yankee, Trademark Collection by Wyndham
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
The price is $144 per night from May 8 to May 9
$144
includes taxes & fees
$129 per night
May 8 - May 9
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,801 reviews)
"It was off season and quiet. Great price :)"

Reviewed on May 3, 2025

Vacation Village in the Berkshires
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

Mitsubishi Mirage or similar
  • 4 people
  • Unlimited mileage
Albany, New York, USA
Mitsubishi Mirage

$50

$200 total
found 6 days ago
Economy Mitsubishi Mirage

Compact

Nissan Versa or similar
  • 5 people
  • Unlimited mileage
Albany, New York, USA
Nissan Versa

$50

$200 total
found 6 days ago
Compact Nissan Versa

Midsize

Toyota Corolla or similar
  • 5 people
  • Unlimited mileage
Albany, New York, USA
Toyota Corolla

$51

$204 total
found 6 days ago
Midsize Toyota Corolla

Standard

Volkswagen Jetta or similar
  • 5 people
  • Unlimited mileage
Albany, New York, USA
Volkswagen Jetta

$53

$212 total
found 6 days ago
Standard Volkswagen Jetta
Lowest prices found within the past 6 days. Prices and availability subject to change. Additional terms may apply.

Berkshire County

Finding cheap flights to Berkshire County is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Berkshire County flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Berkshire County through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Berkshire County—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Berkshire County flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Berkshire County with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

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 $69 to $1,483 this last week. The cheapest one-way ticket prices were $35, 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

More Popular Airlines

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.