Cheap Flight Deals to Great Barrington 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 Great Barrington?

The cheapest prices found with in the last 7 days for return flights were CA $209 and CA $221 for one-way flights to Great Barrington for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
FLLWindsor LocksDecember 27 to January 7CA $209
FLLLathamJanuary 8 to January 15CA $233
MCOWindsor LocksDecember 13 to December 15CA $248
TPAWindsor LocksDecember 17 to December 19CA $253
MCOLathamDecember 20 to January 2CA $310
DCAWindsor LocksNovember 29 to December 7CA $453
ORDWindsor LocksDecember 4 to December 11CA $618
ATLWindsor LocksNovember 28 to December 1CA $853
LAXWindsor LocksDecember 6 to December 7CA $1,039
*Prices include taxes and fees

Your guide to flights to Great Barrington, MA

American Airlines fly to Great Barrington, 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 Great Barrington MA currently costs between CA $209 and CA $1,039. Prices vary, but for the best fares, travel in December when prices are at their lowest.  

Top tips for finding cheap flights to Great Barrington  

The cheapest flight for a round trip to Great Barrington is currently CA $209. When you search for flights to Great Barrington, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Great Barrington for nearby days.  The cheapest month to travel to Great Barrington is December 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 Great Barrington 

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 Great Barrington with Travelocity 

We have top deals on plane tickets even for last minute flights to Great Barrington, 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 Great Barrington for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Great Barrington

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
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
The price is CA $93 per night from Nov. 24 to Nov. 25
CA $93
CA $104 total
includes taxes & fees
24 Nov - 25 Nov
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
8.8/10 Excellent! (678 reviews)
"Nice people operating a very clean, comfortable motel. A bargain."

Reviewed on 17 Nov. 2024

Monument Mountain Motel
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is CA $99 per night from Dec. 4 to Dec. 5
CA $99
CA $111 total
includes taxes & fees
4 Dec - 5 Dec
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,000 reviews)
"The young man who worked the Saturday evening shift until 11 ,was a true gentleman"

Reviewed on 18 Nov. 2024

Quality Inn
Save an average of 15% on thousands of hotels when you're signed in
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
400 Stockbridge Rd, Great Barrington, MA
The price is CA $96 per night from Dec. 1 to Dec. 2
CA $96
CA $108 total
includes taxes & fees
1 Dec - 2 Dec
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (511 reviews)
"Not many tv channels to select from"

Reviewed on 3 Nov. 2024

Travelodge by Wyndham Great Barrington Berkshires
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 Great Barrington

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
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
400 Stockbridge Rd, Great Barrington, MA
The price is CA $96 per night from Dec. 1 to Dec. 2
CA $96
CA $108 total
includes taxes & fees
1 Dec - 2 Dec
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (511 reviews)
"Not many tv channels to select from"

Reviewed on 3 Nov. 2024

Travelodge by Wyndham Great Barrington Berkshires
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
The price is CA $93 per night from Nov. 24 to Nov. 25
CA $93
CA $104 total
includes taxes & fees
24 Nov - 25 Nov
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
8.8/10 Excellent! (678 reviews)
"Nice people operating a very clean, comfortable motel. A bargain."

Reviewed on 17 Nov. 2024

Monument Mountain Motel
Save an average of 15% on thousands of hotels when you're signed in
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is CA $99 per night from Dec. 4 to Dec. 5
CA $99
CA $111 total
includes taxes & fees
4 Dec - 5 Dec
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,000 reviews)
"The young man who worked the Saturday evening shift until 11 ,was a true gentleman"

Reviewed on 18 Nov. 2024

Quality 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 Great Barrington

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
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
The price is CA $212 per night from Nov. 24 to Nov. 25
CA $212
CA $237 total
includes taxes & fees
24 Nov - 25 Nov
Book a stay at this family-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (672 reviews)
"Great hotel with nice staff and facilities. Close to grocery, restaurants and Stockbridge tourist attractions."

Reviewed on 26 Oct. 2024

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
400 Stockbridge Rd, Great Barrington, MA
The price is CA $96 per night from Dec. 1 to Dec. 2
CA $96
CA $108 total
includes taxes & fees
1 Dec - 2 Dec
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (511 reviews)
"Not many tv channels to select from"

Reviewed on 3 Nov. 2024

Travelodge by Wyndham Great Barrington Berkshires
Save an average of 15% on thousands of hotels when you're signed in
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is CA $99 per night from Dec. 4 to Dec. 5
CA $99
CA $111 total
includes taxes & fees
4 Dec - 5 Dec
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,000 reviews)
"The young man who worked the Saturday evening shift until 11 ,was a true gentleman"

Reviewed on 18 Nov. 2024

Quality 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.

Best Great Barrington Flight and Hotel Packages

Great Barrington flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Cobleskill NY
South Shire
Valley Craft Ales
Don't see what you're looking for?
See all available trips from Montreal to Great Barrington
View all trips

Great Barrington flight + hotel packages - business class flights

Price found within the past 48 hours. Click for updated prices.
South Shire
The Equinox Golf Resort & Spa
The Four Chimneys Inn
Don't see what you're looking for?
See all available trips from Toronto to Great Barrington
View all trips

Need a car after flight to Great Barrington?

Frequently asked questions

Which airlines fly to Great Barrington?
Get comfortable in your seatand take to the airaboard one of the11airlines that fly into Great Barrington.Some of the most respectable carriersare:

  • American Airlines
  • Delta Air Lines
  • Southwest Airlines

What airport is best to fly into Great Barrington?
Who enjoys getting caught up in traffic jams while rushing to a flight on the opposite side of the city? Be smart. Great Barrington is home to quite a few airports, so think about which one is closest to where you’re staying. These are the city’s major airports:

  • Bradley International Airport – 64 kilometers from downtown
  • Albany International Airport – 72 kilometers from downtown
  • HFD – 72 kilometers from downtown

Where to stay in Great Barrington
Every extraordinary journey begins with just one step — as well as a nice place to lay your weary head! Lock in your Great Barrington accommodations through Travelocity and you’ll have 286 options to select from.Eager for a taste of the high life on your vacation? Lock in a lavish room with fancy extras at the The Barrington. If you’d rather be more economical with your accommodations, consider a budget property like the Days Inn by Wyndham Great Barrington.
Places to visit in Great Barrington
0 Seeking some more options? 0 But that’s not all. 0
How to get through airport security fast when traveling to Great Barrington
Make your flight to Great Barrington that little bit easier by following these handy security tips:

  • Ensure your boarding pass and travel ID are not hard to access. You will be asked to show them straightaway.
  • You’ll have to place your music on pause for a little while. Headphones need to be removed and put in a tub for X-raying. The same goes for items such as heavy jackets and belts.
  • Electronics such as phones, laptops and cameras need to be put through the X-ray machine separately. Be sure they’re easily accessible.
  • When you approach the security checkpoint, you’ll be asked to put all creams, liquids and gels in a separate tray for scanning. Make sure they’re all in containers no larger than 3.4 ounces (100 milliliters) and sealed in a clear zip-lock bag.
  • Give some thought to the type of footwear you want to fly in. Slippers are awesome because they’re a cinch to slip out of when you’re at the security checkpoint. Try wearing some on your next flight!
  • Stash any multi-tools or other dangerous items inside your checked luggage. Security personnel don’t permit these aboard the aircraft.

Plane Tickets To Great Barrington

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Great Barrington. Browse through our inventory to explore a wide range of cheap flights to Great Barrington to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Great Barrington as you anxiously await to exit the plane and explore what Great Barrington has to offer. Considering all the amazing local food and culture in Great Barrington, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Great Barrington to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Great Barrington without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Great Barrington with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Great Barrington 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.