$29 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 $29 One Way, $38 Round Trip

$38 return flights and $29 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, Feb 7 - Sun, Feb 8
MCO
Orlando
BDL
Hartford
$38 Roundtrip, found 4 days ago
$38
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Feb 7 from Orlando to Hartford, returning Sun, Feb 8, priced at $38 found 4 days ago
Fri, Jan 23 - Mon, Jan 26
MCO
Orlando
BDL
Hartford
$79 Roundtrip, found 2 days ago
$79
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 23 from Orlando to Hartford, returning Mon, Jan 26, priced at $79 found 2 days ago
Fri, Feb 6 - Mon, Feb 9
RDU
Raleigh
BDL
Hartford
$89 Roundtrip, found 2 days ago
$89
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Feb 6 from Raleigh to Hartford, returning Mon, Feb 9, priced at $89 found 2 days ago
Thu, Jan 22 - Sun, Jan 25
RDU
Raleigh
ALB
Albany
$92 Roundtrip, found 13 hours ago
$92
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Thu, Jan 22 from Raleigh to Albany, returning Sun, Jan 25, priced at $92 found 13 hours ago
Sun, Feb 1 - Thu, Feb 5
MCO
Orlando
ALB
Albany
$109 Roundtrip, found 4 days ago
$109
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, Feb 1 from Orlando to Albany, returning Thu, Feb 5, priced at $109 found 4 days ago
Thu, Mar 19 - Mon, Mar 23
MCO
Orlando
BDL
Hartford
$137 Roundtrip, found 20 hours ago
$137
Roundtrip
found 20 hours ago
Select Southwest Airlines flight, departing Thu, Mar 19 from Orlando to Hartford, returning Mon, Mar 23, priced at $137 found 20 hours ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
RSWWindsor LocksJanuary 9 to January 19$171
JFKWindsor LocksJanuary 10 to January 17$195
RSWLathamJanuary 10 to January 20$337
JFKLathamJanuary 9 to January 10$580
*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
$126 nightly
The price is $141 total per night from Jan 6 to Jan 7
$141 total
Jan 6 - Jan 7
Total with taxes and fees
Book a stay at this 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! (2,195 reviews)
No frills stay with a kitchen and dishwasher (make sure your room has one— some do not!!!). Location is across the street from Jiminy Peak, so skiing can be accomplished almost as easy as staying on their property. This is our fourth time staying and it always serves its purpose.

Reviewed on Dec 30, 2025

Opens in a new windowVacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$116 nightly
The price is $130 total per night from Feb 2 to Feb 3
$130 total
Feb 2 - Feb 3
Total with taxes and fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,002 reviews)
friendly accommodating staff

Reviewed on Jan 1, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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
$98 nightly
The price is $109 total per night from Jan 9 to Jan 10
$109 total
Jan 9 - Jan 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,003 reviews)
Staff was very pleasant and friendly. From front desk to valet.

Reviewed on Jan 1, 2026

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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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
$106 nightly
The price is $119 total per night from Jan 13 to Jan 14
$119 total
Jan 13 - Jan 14
Total with taxes and fees
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! (1,010 reviews)
All of the above!

Reviewed on Jan 3, 2026

Opens in a new windowThe Yankee, Trademark Collection by Wyndham
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
  • Unlimited mileage
Albany, New York, USA
Chevrolet Spark

$40

$161 total
found 3 days ago
Economy Chevrolet Spark

Standard

Chevrolet Cruze or similar
  • 5 people
  • Unlimited mileage
Albany, New York, USA
Chevrolet Cruze

$41

$164 total
found 3 days ago
Standard Chevrolet Cruze

Compact

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

$41

$165 total
found 3 days ago
Compact Nissan Versa Note

Midsize

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

$42

$168 total
found 3 days ago
Midsize Toyota Corolla
Lowest prices found within the past 3 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.

Innovative Orbitz Tools for the Trip Planner on the Move

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 $38 to $580 this last week. The cheapest one-way ticket prices were $29, 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

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.