Cheap Flight Deals to The Berkshires MA from CA $227

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How to find cheap flights to The Berkshires?

The cheapest prices found with in the last 7 days for return flights were CA $378 and CA $227 for one-way flights to The Berkshires for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
JFKLathamJanuary 7 to January 13CA $492
JFKWindsor LocksJanuary 3 to January 9CA $602
*Prices include taxes and fees

Your guide to flights to The Berkshires, MA

Delta, American Airlines fly to The Berkshires, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to The Berkshires MA currently costs between CA $378 and CA $602. Prices vary, but for the best fares, travel in January when prices are at their lowest.  

Top tips for finding cheap flights to The Berkshires  

The cheapest flight for a round trip to The Berkshires is currently CA $378. When you search for flights to The Berkshires, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to The Berkshires for nearby days.  The cheapest month to travel to The Berkshires is January from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to The Berkshires 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to The Berkshires with Travelocity 

We have top deals on plane tickets even for last minute flights to The Berkshires, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to The Berkshires for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to The Berkshires

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
The price is CA $85 per night from Dec. 26 to Dec. 27
CA $85
CA $93 total
includes taxes & fees
26 Dec - 27 Dec
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.8/10 (955 reviews)
"Well located near attractions"

Reviewed on 29 Oct. 2024

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 CA $99 per night from Dec. 23 to Dec. 24
CA $99
CA $111 total
includes taxes & fees
23 Dec - 24 Dec
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Guido's ...
7/10 Good! (597 reviews)
"Great location. Pleasant staff."

Reviewed on 13 Oct. 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 Housatonic River and Lake Mansfield Park are located ...
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 22 Nov. 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 Jiminy Peak Mountain Resort and Crane Museum of Papermaking ...
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 1 Oct. 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
The price is CA $609 per night from Jan. 2 to Jan. 3
CA $609
CA $737 total
includes taxes & fees
2 Jan - 3 Jan 2025
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesterwood and Norman Rockwell Museum ...
9.2/10 Wonderful! (80 reviews)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer ..."

Reviewed on 27 Jul. 2024

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

The Orchards Hotel

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

Reviewed on 9 Mar. 2020

The Orchards Hotel
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 Housatonic River and Lake Mansfield Park are located ...
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 22 Nov. 2021

Lantern House Motel
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Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
The price is CA $99 per night from Dec. 23 to Dec. 24
CA $99
CA $111 total
includes taxes & fees
23 Dec - 24 Dec
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Guido's ...
7/10 Good! (597 reviews)
"Great location. Pleasant staff."

Reviewed on 13 Oct. 2024

Wagon Wheel Inn
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

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
The price is CA $269 per night from Jan. 1 to Jan. 2
CA $269
CA $310 total
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Our guests praise the helpful staff in our ...
8.6/10 Excellent! (1,748 reviews)
"Nice and quiet family get a way"

Reviewed on 16 Dec. 2024

Vacation Village in the Berkshires
Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
The price is CA $167 per night from Jan. 5 to Jan. 6
CA $167
CA $186 total
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 3-star 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 ...
8.6/10 Excellent! (1,000 reviews)
"Stayed for a weekend wedding and it was a great location. Room was large"

Reviewed on 19 Dec. 2024

Hotel Downstreet
Stay Berkshires

Stay Berkshires

2 out of 5
1146 Cold Spring Road, Williamstown, MA
Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Sterling and Francine Clark Art Institute and The ...
8.2/10 Very Good! (352 reviews)
"Nice option to stay near MASS MOCA."

Reviewed on 4 Dec. 2024

Stay Berkshires
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Williamstown Motel

Williamstown Motel

2 out of 5
295 Main Street, Route 2, Williamstown, MA
The price is CA $153 per night from Jan. 22 to Jan. 23
CA $153
CA $171 total
includes taxes & fees
22 Jan - 23 Jan 2025
Book a stay at this business-friendly motel in Williamstown. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the ...
8.4/10 Very Good! (589 reviews)
"Owner was very friendly. Room were roomy. Clean"

Reviewed on 20 Dec. 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

Price found within the past 48 hours. Click for updated prices.
Aspen At Manchester
The Equinox Golf Resort & Spa
Kimpton Taconic Hotel, an IHG Hotel
Don't see what you're looking for?
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Need a car after flight to The Berkshires?

Frequently asked questions

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 CA $378. 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, January 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 CA $378. 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 CA $378 and CA $602 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.

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.