Cheap Flights to The Berkshires from $44

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How Much Does it Cost To Fly To The Berkshires?

The cheapest prices found with in the last 7 days for return flights were $155 and $44 for one-way flights to The Berkshires for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
IADWindsor LocksMarch 31 to April 2$449
*Prices include taxes and fees

The Berkshires BDL Flight Information

Traveling to
The Berkshires BDL
Lowest Price
$155
Number of Airlines Serving
2
Airlines Serving
Frontier Airlines, Spirit Airlines, American Airlines
Number of Daily Flights
7
Airlines with Direct Flights
American Airlines, Alaska Airlines

Find The Perfect Hotel For After Your Flight

Amazing The Berkshires Accommodation Deals

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
The price is $56 per night from Apr 1 to Apr 2
$56
per night
Apr 1 - Apr 2
Stay at this business-friendly motel in West Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6.8/10 (897 reviews)
"Always great!"

Reviewed on Dec 12, 2023

Pleasant Valley Motel West Stockbridge
Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
The price is $69 per night from Mar 29 to Mar 30
$69
per night
Mar 29 - Mar 30
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
7/10 Good! (545 reviews)
"Maintenance services / quick to respond"

Reviewed on Feb 19, 2024

Wagon Wheel Inn
Lantern House Motel

Lantern House Motel

2.5 out of 5
256 Stockbridge Road, Great Barrington, MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions National Shrine of the Divine Mercy and Housatonic ...
8.2/10 Very Good! (454 reviews)
Avoid staying here if you can.
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ..."

Reviewed on Nov 22, 2021

Lantern House Motel
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The Weathervane Motel

The Weathervane Motel

2 out of 5
475 South Main St. Route 7, Lanesborough, MA
Stay at this motel in Lanesborough. Enjoy free WiFi, free parking, and a garden. Popular attractions Crane Museum of Papermaking and Barrington Stage Company ...
7/10 Good! (128 reviews)
"Booked a king bed but when I got there they told me no cable in that room. They gave me a room with a double bed that were on top of being small were very uncomfortable plus so much dust in air conditioner my allergies were affected plus it stunk couldn’t stay had to repack and go drive around and ..."

Reviewed on Oct 1, 2020

The Weathervane Motel
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.

Luxury Hotels in The Berkshires

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions National Shrine of the Divine Mercy and ...
9.2/10 Wonderful! (75 reviews)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."

Reviewed on Oct 12, 2023

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Orchards Hotel

The Orchards Hotel

3.5 out of 5
222 Adams Rd, Williamstown, MA
Stay at this 3.5-star business-friendly hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hopkins Observatory and ...
8.4/10 Very Good! (441 reviews)
"A little dated. Restaurant shut down for renovations, disappointing"

Reviewed on Mar 9, 2020

The Orchards Hotel
Federal House Inn

Federal House Inn

3.5 out of 5
1560 Pleasant Street, Route 102, South Lee, MA
Stay at this 3.5-star B&B in South Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Berkshire Theatre Festival and Schantz Galleries ...
9.6/10 Exceptional! (177 reviews)
"Wine, cheese and crackers every night. A three course breakfast every morning. A 24 hour a day kitchen stocked with complimentary sodas, water, coffee, tea, and ice. Great fireplace in the room. The owner was very accommodating. Even before we got there we received a call from him inviting us to ..."

Reviewed on Dec 4, 2019

Federal House Inn
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Lantern House Motel

Lantern House Motel

2.5 out of 5
256 Stockbridge Road, Great Barrington, MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions National Shrine of the Divine Mercy and Housatonic ...
8.2/10 Very Good! (454 reviews)
Avoid staying here if you can.
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ..."

Reviewed on Nov 22, 2021

Lantern House Motel
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.

Family Friendly Hotels in The Berkshires

Vacation Village in the Berkshires
Great for families

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
The price is $169 per night from Mar 29 to Mar 30
$169
per night
Mar 29 - Mar 30
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free WiFi, free parking, and a children's pool. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,662 reviews)

Families like: Kids pool, kitchen, playground, game room

Travelers say...
"Clean and spacious!"

Reviewed on Mar 4, 2024

Vacation Village in the Berkshires
Hotel Downstreet
Great for families

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
The price is $159 per night from Mar 31 to Apr 1
$159
per night
Mar 31 - Apr 1
Stay at this hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our ...
8.4/10 Very Good! (895 reviews)

Families like: Indoor pools, game room, skiing nearby, games and toys

Travelers say...
"Very nice staff, very clean! The pool is in the basement and feels like an old YMCA- clean but kind of creepy feeling and loud door to a large fan being run. The rooms are clean but dark! And the sheets are not cotton so that’s not great for a good nights sleep."

Reviewed on Mar 21, 2024

Hotel Downstreet
Stay Berkshires
Great for families

Stay Berkshires

2.5 out of 5
1146 Cold Spring Road, Williamstown, MA
The price is $160 per night from Mar 29 to Mar 30
$160
per night
Mar 29 - Mar 30
Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Sterling and Francine Clark Art Institute and The ...
8.4/10 Very Good! (335 reviews)

Families like: Outdoor pool, free breakfast for the whole family

Travelers say...
"The staff went to great lengths to solve a problem that arose with my reservation. I would strongly recommend Stay Berkshire for a visit to the Williamstown area."

Reviewed on Oct 9, 2023

Stay Berkshires
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Williamstown Motel
Great for families

Williamstown Motel

2 out of 5
295 Main Street, Route 2, Williamstown, MA
The price is $71 per night from Mar 31 to Apr 1
$71
per night
Mar 31 - Apr 1
Stay at this business-friendly motel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (541 reviews)

Families like: Skiing nearby, extra beds/cribs, free breakfast for the whole family, laundry

Travelers say...
"The owner, Rocky, was very warm and hospitable. He offered quality dining recommendations, and made me feel welcomed."

Reviewed on Mar 23, 2024

Williamstown Motel
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.

Best The Berkshires Flight and Hotel Packages

The Berkshires flight + hotel packages - economy flights

Equinox Resort Residences
The Equinox Golf Resort & Spa
The White House Inn
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Prices and availability subject to change. Additional terms may apply.

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Frequently asked questions

Can I fly to The Berkshires right now?
Travel restrictions are always evolving, so research relevant official government websites for information before booking your fare. Whether you can hop on a flight to The Berkshires will depend on a range of factors, such as where you’re flying from and current COVID-19 restrictions. Another handy source of info is our Covid-19 Travel Advisor. It features guidance on social distancing, testing requirements, quarantine rules and more for your destination.
How much is the cheapest flight to The Berkshires?
The next vacation you take doesn’t have to make a huge dent in your finances. During the last seven days, the cheapest roundtrip flight to The Berkshires cost $155. Find a cheap fare and spend the cash you save on cool experiences. This price was available on Travelocity for flights to The Berkshires departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to The Berkshires?
If you’ve been daydreaming about a getaway in The Berkshires, April is the cheapest month to hop on a plane. This is based on Travelocity’s direct return flight demand between January and December last year. Work out your ideal dates and lock in your flights today.
How can I check my flight status to The Berkshires?
Check for updates on your flight to The Berkshires, make changes to your journey and loads more from our useful Trips portal. Located at the top of the Travelocity homepage, it’s your one-stop shop for viewing and managing your bookings. Just log in or create a new account in seconds. Savvy adventurers will also enjoy the Travelocity app. You’ll get real-time travel updates, as well as the ability to view deals on hotels, rental cars and activities while you’re out and about. If you have friends or family flying with you, it’s also a convenient way to share your flight details with each other.
How do I find the best deals on flights to The Berkshires?
Be flexible with your travel dates and there’s a good chance you’ll find a sensational deal. When searching for flights on Travelocity, click the “Flexible dates” box above your results to compare prices with nearby days. Also try to book in advance and avoid vacation periods. In the last seven days, the best price for a roundtrip flight to The Berkshires was $155. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to The Berkshires with Travelocity?
Check out cheap flights to The Berkshires with Travelocity and begin packing for your next adventure. With round-the-clock customer support during every stage of your trip and our Price Match Guarantee, we take the hassle out of reserving cheap family flights, hotels, rental cars and more. Snag an awesome deal today and prepare for the adventure of a lifetime.
What are the most popular flight routes to The Berkshires?
Whether you’re thinking about a short trip or a long escape, we can help you book your ideal flight to The Berkshires. Major flight routes to this destination include:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 1,131 flights a month.
  • Chicago, IL (ORD-O’Hare Intl.) to Bradley Intl. Airport (BDL) - 1,048 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 866 flights a month.

How much is a flight to The Berkshires on average?
Airfares for roundtrip flights to The Berkshires were priced between $155 and $449 in the last seven days. The moment you see a great deal, lock it in and get ready to embark on the getaway of your dreams with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to The Berkshires?
Below are a handful of major direct flights to The Berkshires with their average journey times:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 15 minutes
  • Chicago, IL (ORD-O’Hare Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 9 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 1 hour and 12 minutes

What can I expect on a flight to The Berkshires?
This will mostly depend on your departure point and which air carrier you’re traveling with. You’re likely to find all types of flights to The Berkshires, from first class fares to cheap flights for family vacations. If a flight is classed as long haul, the airline will usually provide hot meals and entertainment as well as games for the kids.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.

 

What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.

 

How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Flights To The Berkshires

The Berkshires has a legendary draw for travelers who like their vacations quaint and quiet. Nestled between Massachusetts's Taconic Mountains and the Hudson Highlands, it is the perfect place for people who want to escape the hectic pace of city life. It's a largely rural area with seemingly endless options for outdoor recreation, and plenty of small towns that offer a lot of unique and delicious options for dining. When you fly to The Berkshires, you'll notice the slower pace of life here right away—a pace that has a rejuvenating effect on the minds and bodies of all visitors.

Transportation from PSF

The Berkshires flights land at Pittsfield Municipal Airport (PSF) in Berkshire County. Considering that this is a largely rural area, there aren't many public transportation options. You can call for a taxi while you find your luggage, or you can get a car at one of several nearby rental agencies. Some local hotels offer shuttle service to and from the airport for their guests; you can contact hotels in The Berkshires to see which ones offer this option. After you get settled in at your hotel, you may want to visit a restaurant for some nourishment. Thankfully., there are plenty of excellent places to dine in Monterey and New Marlborough. You may choose an option that's near your hotel—that way, you can start your vacation with a relaxing, no-fuss meal.

Enjoy the Culture and Beauty of The Berkshires

When you choose The Berkshires as your next vacation destination, you'll have seemingly endless fun activities to consider. There are wonderful art museums in Stockbridge, North Adams, and Williamstown. If you like wandering through nature, you can visit any of the beautiful local parks and stunning preserves. By booking vacations in The Berkshires here at Travelocity, you can save up to $537, leaving you with plenty of money to enjoy any activity in The Berkshires that catches your attention. Make your travel plans today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.