$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, $56 Round Trip

$56 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.

Fri, Feb 13 - Sun, Feb 22
MCO
Orlando
BDL
Hartford
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Feb 13 from Orlando to Hartford, returning Sun, Feb 22, priced at $56 just found
Fri, Jan 30 - Mon, Feb 2
CHS
Charleston
ALB
Albany
$82 Roundtrip, found 22 hours ago
$82
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, Jan 30 from Charleston to Albany, returning Mon, Feb 2, priced at $82 found 22 hours ago
Thu, Feb 5 - Sun, Feb 8
CHS
Charleston
BDL
Hartford
$93 Roundtrip, found 9 hours ago
$93
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Feb 5 from Charleston to Hartford, returning Sun, Feb 8, priced at $93 found 9 hours ago
Tue, Jan 20 - Thu, Jan 22
RDU
Raleigh
ALB
Albany
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jan 20 from Raleigh to Albany, returning Thu, Jan 22, priced at $100 found 1 day ago
Fri, Feb 27 - Mon, Mar 2
TPA
Tampa
BDL
Hartford
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Feb 27 from Tampa to Hartford, returning Mon, Mar 2, priced at $107 found 1 day ago
Wed, Jan 28 - Mon, Feb 2
RDU
Raleigh
BDL
Hartford
$109 Roundtrip, found 3 days ago
$109
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Jan 28 from Raleigh to Hartford, returning Mon, Feb 2, priced at $109 found 3 days ago
Thu, Feb 5 - Mon, Feb 9
MCO
Orlando
ALB
Albany
$125 Roundtrip, found 2 days ago
$125
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Feb 5 from Orlando to Albany, returning Mon, Feb 9, priced at $125 found 2 days ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
RSWWindsor LocksJanuary 18 to January 30$278
RSWLathamJanuary 17 to January 28$378
JFKLathamJanuary 18 to January 27$591
*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 19 to Jan 20
$141 total
Jan 19 - Jan 20
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! (2,202 reviews)
Clean rooms, chimney did not work

Reviewed on Jan 4, 2026

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
$125 nightly
The price is $140 total per night from Feb 2 to Feb 3
$140 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! (1,000 reviews)
Staff was pleasant and helpful, room spacey and all immaculate .

Reviewed on Jan 11, 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 23 to Jan 24
$109 total
Jan 23 - Jan 24
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! (1,000 reviews)
Staff was very courteous and rooms clean.

Reviewed on Jan 12, 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
$93 nightly
The price is $103 total per night from Jan 25 to Jan 26
$103 total
Jan 25 - Jan 26
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! (1,001 reviews)
Everything was great!

Reviewed on Jan 8, 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

$49

$164 total
found 5 days ago
Economy Chevrolet Spark

Standard

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

$49

$163 total
found 5 days ago
Standard Chevrolet Cruze

Compact

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

$50

$168 total
found 5 days ago
Compact Nissan Versa Note

Midsize

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

$51

$170 total
found 5 days ago
Midsize Toyota Corolla
Lowest prices found within the past 5 days. Prices and availability subject to change. Additional terms may apply.

Berkshire County

Start your search for cheap flights to Berkshire County on Orbitz. Orbitz is where you will discover guaranteed low prices on Berkshire County flights, as well as all of the following conveniences:

Travel Updates on Your Mobile Device

Orbitz offers cutting-edge mobile tools for your smartphone. Whether you own an iPhone or an Android phone, you can benefit from Orbitz’s flight status updates and even book your future Berkshire County flights. You can also review and reserve hotel rooms for when your Berkshire County flights land and see other special offers.

Low Prices Guaranteed on Flights to Berkshire County

Orbitz offers large discounts on a wide range of Berkshire County flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Berkshire County while taking advantage of the lowest fares around.

Customer Care When You Need It

Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Berkshire County to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.

Loyalty Program Participation Opportunities

Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Berkshire County. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.

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 $56 to $591 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.