$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, $62 Round Trip

$62 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.

Thu, Apr 30 - Sat, May 2
MCO
Orlando
BDL
Hartford
$62 Roundtrip, found 1 day ago
$62
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Orlando to Hartford, returning Sat, May 2, priced at $62 found 1 day ago
Sun, Sep 6 - Fri, Sep 11
RDU
Raleigh
ALB
Albany
$97 Roundtrip, found 4 days ago
$97
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, Sep 6 from Raleigh to Albany, returning Fri, Sep 11, priced at $97 found 4 days ago
Thu, Sep 10 - Sun, Sep 13
RDU
Raleigh
BDL
Hartford
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 10 from Raleigh to Hartford, returning Sun, Sep 13, priced at $122 found 1 day ago
Thu, Apr 30 - Tue, May 12
MCO
Orlando
ALB
Albany
$128 Roundtrip, just found
$128
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Apr 30 from Orlando to Albany, returning Tue, May 12, priced at $128 just found
Sat, May 23 - Sat, May 30
RSW
Fort Myers
ALB
Albany
$132 Roundtrip, just found
$132
Roundtrip
just found
Select Breeze Airways flight, departing Sat, May 23 from Fort Myers to Albany, returning Sat, May 30, priced at $132 just found
Sat, Jun 6 - Sun, Jun 14
RSW
Fort Myers
BDL
Hartford
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Jun 6 from Fort Myers to Hartford, returning Sun, Jun 14, priced at $142 found 1 day ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
JFKLathamMarch 1 to March 10$295
RSWWindsor LocksFebruary 28 to March 2$300
RSWLathamFebruary 28 to March 4$304
JFKWindsor LocksFebruary 27 to March 3$312
*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
$126 nightly
The price is $141 total per night from Feb 24 to Feb 25
$141 total
Feb 24 - Feb 25
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 ...
8.8/10 Excellent! (2,261 reviews)
Clean room. Spacious.

Reviewed on Feb 22, 2026

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
$121 nightly
The price is $136 total per night from Mar 24 to Mar 25
$136 total
Mar 24 - Mar 25
Total with taxes and fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (859 reviews)
Second stay. Great as usual!

Reviewed on Feb 22, 2026

Opens in a new windowBerkshire Mountain Lodge
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
$181 nightly
The price is $203 total per night from Feb 24 to Feb 25
$203 total
Feb 24 - Feb 25
Total with taxes and fees
Book a stay at this 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! (579 reviews)
This hotel is clean, modernized and close to Williamstown POI.

Reviewed on Feb 22, 2026

Opens in a new windowThe Williams Inn
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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
$93 nightly
The price is $103 total per night from Mar 2 to Mar 3
$103 total
Mar 2 - Mar 3
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 ...
9.2/10 Wonderful! (1,013 reviews)
Clean room nice staff

Reviewed on Feb 22, 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
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

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First-Timers

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Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to Berkshire County and Berkshire County flights. Get more bang for your travel buck at Orbitz.

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 $62 to $312 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.