$51 Cheap flights to Berkshire County

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Top places to visit in Berkshire County

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Lenox

Lenox

Cheap flights to Berkshire County from $51 One Way, $67 Round Trip

$67 return flights and $51 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 - Sun, May 3
MCO
Orlando
BDL
Hartford
$67 Roundtrip, found 2 days ago
$67
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Orlando to Hartford, returning Sun, May 3, priced at $67 found 2 days ago
Fri, Aug 21 - Fri, Aug 28
RDU
Raleigh
ALB
Albany
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 21 from Raleigh to Albany, returning Fri, Aug 28, priced at $97 found 2 days ago
Fri, Aug 28 - Sat, Sep 5
RDU
Raleigh
BDL
Hartford
$112 Roundtrip, found 2 days ago
$112
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 28 from Raleigh to Hartford, returning Sat, Sep 5, priced at $112 found 2 days ago
Wed, Aug 26 - Wed, Sep 2
TPA
Tampa
BDL
Hartford
$142 Roundtrip, found 6 days ago
$142
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Tampa to Hartford, returning Wed, Sep 2, priced at $142 found 6 days ago
Fri, May 1 - Mon, May 4
FLL
Fort Lauderdale
BDL
Hartford
$163 Roundtrip, found 3 days ago
$163
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, May 1 from Fort Lauderdale to Hartford, returning Mon, May 4, priced at $163 found 3 days ago
Thu, Apr 30 - Tue, May 5
MCO
Orlando
ALB
Albany
$173 Roundtrip, found 5 days ago
$173
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Apr 30 from Orlando to Albany, returning Tue, May 5, priced at $173 found 5 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
JFKWindsor LocksApril 12 to April 17$329
RSWWindsor LocksApril 12 to April 13$446
RSWLathamApril 11 to April 15$485
*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 Apr 12 to Apr 13
$141 total
Apr 12 - Apr 13
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! (2,328 reviews)
great stay.

Reviewed on Apr 9, 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
$127 nightly
The price is $142 total per night from May 10 to May 11
$142 total
May 10 - May 11
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 ...
8.8/10 Excellent! (1,001 reviews)
Nice staff comfy bed nice views

Reviewed on Apr 8, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from May 10 to May 11
$120 total
May 10 - May 11
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! (897 reviews)
Love that place. Does need a little sprucing up. Staff great and accomodating

Reviewed on Apr 5, 2026

Opens in a new windowBerkshire Mountain Lodge
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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
$103 nightly
The price is $115 total per night from Apr 12 to Apr 13
$115 total
Apr 12 - Apr 13
Total with taxes and fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (892 reviews)
We did not see a pool

Reviewed on Apr 8, 2026

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

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You can now book flights to Berkshire County on the new cutting-edge mobile tool for Android or iPhone users. Hotel packages, flight updates and changes can all be accessed using this tool. When you make any reservations or bookings using this service, confirmation will be provided on the same day the request was made. Take advantage of Orbitz friendly service and low cost Berkshire County flights.

Discounted tickets available for flights to Berkshire County

Orbitz offers tickets at a discounted, budget friendly rate that will satisfy all of your travel requirements. Book your Berkshire County flights with us and structure a package that includes car hire, family activities and cheap accommodation. Orbitz will ensure that all your requirements are met, letting you relax and enjoy your holiday as it was intended.

Orbitz offers discounted Berkshire County flights

Discounted flights to Berkshire County ensure that all who want to travel can Take advantage of Orbitz’ guaranteed low prices and affordable packages. You will enjoy a hassle free trip, an up to date travel planner and friendly service.

Traveler profile updates

When flying with Orbitz, take advantage of frequent updates on your flights to Berkshire County. Details and updates are sent to up to six contact numbers to ensure that you are kept abreast of the latest information on Berkshire County flights. Frequent flyer and loyalty membership numbers may be updated within your Orbitz account profile.

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 $67 to $485 this last week. The cheapest one-way ticket prices were $51, originating in Raleigh (RDU).
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.