Cheap Flight Deals to The Berkshires MA from CA $221

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How to find cheap flights to The Berkshires?

The cheapest prices found with in the last 7 days for return flights were CA $367 and CA $221 for one-way flights to The Berkshires for the period specified. Prices and availability are subject to change. Additional terms apply

Your guide to flights to The Berkshires, MA

Delta, Air Canada 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 $367 and CA $367. Prices vary, but for the best fares, travel in June 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 $367. 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 May 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 $95 per night from May 19 to May 20
CA $95
per night
May 19 - May 20
Book a 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 ...
6.8/10 (901 reviews)
"Great stay for the price"

Reviewed on 6 Apr. 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 $94 per night from May 19 to May 20
CA $94
per night
May 19 - May 20
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! (546 reviews)
"Deff stay again if in the area"

Reviewed on 26 Apr. 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 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 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 $549 per night from May 12 to May 13
CA $549
per night
May 12 - May 13
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
9.2/10 Wonderful! (76 reviews)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."

Reviewed on 12 Oct. 2023

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
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 Tanglewood Music Center and Berkshire Theatre ...
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 4 Dec. 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 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
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

Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
The price is CA $204 per night from May 19 to May 20
CA $204
per night
May 19 - May 20
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! (915 reviews)
"In the heart of downtown North Adams, we could leave and walk around, shop, get coffee. Our room on the 6th floor overlooked Main Street. It was a beautiful Mountain view & of the Four Church Steeples. The vintage Lampposts that lined Main St. and up over the bridge were just a beautiful bonus lighting ..."

Reviewed on 5 May 2024

Hotel Downstreet
Stay Berkshires

Stay Berkshires

2.5 out of 5
1146 Cold Spring Road, Williamstown, MA
The price is CA $219 per night from May 21 to May 22
CA $219
per night
May 21 - May 22
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)
"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 9 Oct. 2023

Stay Berkshires
Williamstown Motel

Williamstown Motel

2 out of 5
295 Main Street, Route 2, Williamstown, MA
The price is CA $95 per night from May 12 to May 13
CA $95
per night
May 12 - May 13
Book a 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 ...
8.4/10 Very Good! (546 reviews)
"Perfectly fine motel."

Reviewed on 5 May 2024

Williamstown Motel
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Cozy Corner Motel

Cozy Corner Motel

2 out of 5
284 Sand Springs Rd. Rte 7, Williamstown, MA
The price is CA $103 per night from May 19 to May 20
CA $103
per night
May 19 - May 20
Book a stay at this family-friendly motel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (679 reviews)
"The only place we stay when we come to town! The owner could not be any nicer. The rooms are great, the area quiet, and the breakfast, delicious."

Reviewed on 8 May 2024

Cozy Corner 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.

Need a car after flight to The Berkshires?

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 CA $367. 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, May 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 $367. 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 $367 and CA $367 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 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.