$31 Cheap flights to Berkshire County

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Cheap flights to Berkshire County from $31 One Way, $99 Round Trip

$99 return flights and $31 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.

Wed, Dec 10 - Sun, Dec 14
MCO
Orlando
BDL
Hartford
$99 Roundtrip, found 6 days ago
$99
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Dec 10 from Orlando to Hartford, returning Sun, Dec 14, priced at $99 found 6 days ago
Thu, Dec 11 - Tue, Dec 16
RDU
Raleigh
ALB
Albany
$102 Roundtrip, found 12 hours ago
$102
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Thu, Dec 11 from Raleigh to Albany, returning Tue, Dec 16, priced at $102 found 12 hours ago
Fri, Oct 31 - Mon, Nov 3
TPA
Tampa
BDL
Hartford
$102 Roundtrip, found 2 hours ago
$102
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Fri, Oct 31 from Tampa to Hartford, returning Mon, Nov 3, priced at $102 found 2 hours ago
Fri, Nov 7 - Mon, Nov 10
MCO
Orlando
BDL
Hartford
$112 Roundtrip, found 3 days ago
$112
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Orlando to Hartford, returning Mon, Nov 10, priced at $112 found 3 days ago
Fri, Dec 5 - Sun, Dec 7
RDU
Raleigh
BDL
Hartford
$118 Roundtrip, found 15 hours ago
$118
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, Dec 5 from Raleigh to Hartford, returning Sun, Dec 7, priced at $118 found 15 hours ago
Thu, Dec 11 - Mon, Dec 15
MCO
Orlando
BDL
Hartford
$123 Roundtrip, just found
$123
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Dec 11 from Orlando to Hartford, returning Mon, Dec 15, priced at $123 just found
Thu, Nov 13 - Sun, Nov 16
MCO
Orlando
ALB
Albany
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 13 from Orlando to Albany, returning Sun, Nov 16, priced at $127 found 1 day ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
JFKWindsor LocksOctober 12 to October 15$111
RSWWindsor LocksOctober 11 to October 12$351
RSWLathamOctober 12 to October 21$452
JFKLathamOctober 11 to October 21$629
*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
$112 nightly
The price is $125 total per night from Nov 2 to Nov 3
$125 total
Nov 2 - Nov 3
Total with 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! (2,039 reviews)
"There were a couple of issues withy stay 10/4/26 to 10/5/26. The staff did not answer my text messages sent as they said they were very busy. The room has small insects and flies. It was reported and staff offered to send maintenance to check on the unit. I was moved to another unit 10/5/25 through ..."

Reviewed on Oct 7, 2025

Opens in a new windowVacation 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
$97 nightly
The price is $108 total per night from Nov 2 to Nov 3
$108 total
Nov 2 - Nov 3
Total with 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! (678 reviews)
"Great lodge with 1 bedroom suites and fully stocked kitchens"

Reviewed on Oct 7, 2025

Opens in a new windowBerkshire Mountain Lodge
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $144 total per night from Nov 2 to Nov 3
$144 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (749 reviews)
"This is a fun family resort... a great vacation place .. in a great location.. something for everyone. Perfect family reunion place.. All Ages happy.."

Reviewed on Oct 6, 2025

Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $98 total per night from Nov 2 to Nov 3
$98 total
Nov 2 - Nov 3
Total with taxes and fees
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! (743 reviews)
"Parking was easy Everything was great"

Reviewed on Oct 4, 2025

Opens in a new windowBerkshires Untold
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

Save money on your flights to Berkshire County as well as on hotel and car packages.

 

Free Fees

Snap up cheap Berkshire County flights at Orbitz, and pay no booking fees. We also don’t charge fees when your plans change or are cancelled. While you’re there, check out our low fare deals on flights to other locations besides flights to Berkshire County.

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Mix and Match

At Orbitz, we turned a great idea from the world of fashion into another way for you to save money. When you shop our low cost tickets on flights to any destination, don’t be afraid to mix and match different airlines for maximum savings on your Berkshire County flights air ticket. Save more on air travel every day in every way at Orbitz.

Frequently asked questions

Which airlines fly to Berkshire County?
Check your passport is up to date and choose from the 14 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 $99 to $629 this last week. The cheapest one-way ticket prices were $31, 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.

More to Explore

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.