Cheap Flights to Great Barrington from $44

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How Much Does it Cost To Fly To Great Barrington?

The cheapest prices found with in the last 7 days for return flights were $97 and $44 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 LocksAugust 14 to August 28$97
ATLWindsor LocksJune 3 to June 11$108
TPAWindsor LocksAugust 6 to August 27$116
MCOWindsor LocksAugust 27 to August 31$128
ORDWindsor LocksJune 26 to July 2$154
FLLLathamJune 13 to June 16$177
DCALathamJuly 16 to July 24$179
DENWindsor LocksAugust 17 to August 22$180
DCAWindsor LocksJune 12 to June 15$184
SJUWindsor LocksJune 4 to June 11$188
ATLLathamJune 10 to June 11$217
SJULathamAugust 8 to August 26$236
TPALathamAugust 27 to August 31$240
LAXWindsor LocksAugust 13 to August 24$269
LAXLathamAugust 27 to September 12$284
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOWindsor LocksJune 1 to June 8$132
ATLWindsor LocksMay 31 to June 3$165
TPAWindsor LocksJune 2 to June 4$193
MCOLathamMay 31 to June 8$207
SJUWindsor LocksJune 1 to June 4$210
ORDWindsor LocksJune 1 to June 5$216
FLLLathamJune 1 to June 5$246
DENWindsor LocksJune 1 to June 4$256
TPALathamJune 1 to June 15$277
DCAWindsor LocksJune 1 to June 4$298
LAXWindsor LocksJune 2 to June 20$367
SJULathamMay 31 to June 6$399
DENLathamMay 30 to June 11$403
CLTLathamMay 31 to June 15$410
ATLLathamJune 2 to June 6$438
*Prices include taxes and fees

Great Barrington Flight Information

Traveling to
Great Barrington
Lowest Price
$97
Number of Airlines Serving
Airlines Serving
Frontier Airlines, Spirit Airlines
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Great Barrington Accommodation Deals

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 Nov 22, 2021

Lantern House Motel
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
The price is $66 per night from May 27 to May 28
$66
per night
May 27 - May 28
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! (596 reviews)
"Old style motel but spotlessly clean. I was able to walk to a nearby Mexican restaurant that was excellent. Thank you for a pleasant and relaxing stay!"

Reviewed on May 20, 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 $85 per night from May 30 to May 31
$85
per night
May 30 - May 31
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8/10 Very Good! (1,000 reviews)
"Clean . Comfortable for my needs. Staff are friendly and courteous."

Reviewed on May 17, 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 $69 per night from May 27 to May 28
$69
per night
May 27 - May 28
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! (456 reviews)
"Manager was friendly and patient late at night."

Reviewed on May 12, 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 Nov 22, 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 $69 per night from May 27 to May 28
$69
per night
May 27 - May 28
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! (456 reviews)
"Manager was friendly and patient late at night."

Reviewed on May 12, 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 $66 per night from May 27 to May 28
$66
per night
May 27 - May 28
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! (596 reviews)
"Old style motel but spotlessly clean. I was able to walk to a nearby Mexican restaurant that was excellent. Thank you for a pleasant and relaxing stay!"

Reviewed on May 20, 2024

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

The Barrington

4 out of 5
281 Main St., Level 3, Great Barrington, MA
The price is $325 per night from May 27 to May 28
$325
per night
May 27 - May 28
Stay at this 4-star business-friendly B&B in Great Barrington. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Mahaiwe Performing ...
9.6/10 Exceptional! (98 reviews)
Wonderful Stay!
"As always, our stay at The Barrington was wonderful. The rooms are large, lovely and the bed comfortable. The service is great and everyone is so friendly and accommodating! The breakfast is delicious. We truly enjoy our stay, every time!"

Reviewed on May 20, 2024

The Barrington
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
Great for families

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)

Families like: Outdoor pool, playground, extra beds/cribs, free breakfast for the whole family

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
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great for families

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
The price is $152 per night from May 27 to May 28
$152
per night
May 27 - May 28
Book a stay at this family-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (648 reviews)

Families like: Indoor pools, playground, game room, skiing nearby

Travelers say...
"Staff was very friendly. Facilities were clean and comfortable. Breakfast was quite good. Convenient location. We had a terrific stay!"

Reviewed on May 12, 2024

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

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
400 Stockbridge Rd, Great Barrington, MA
The price is $69 per night from May 27 to May 28
$69
per night
May 27 - May 28
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! (456 reviews)

Families like: Skiing nearby, extra beds/cribs, laundry

Travelers say...
"Manager was friendly and patient late at night."

Reviewed on May 12, 2024

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

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is $85 per night from May 30 to May 31
$85
per night
May 30 - May 31
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8/10 Very Good! (1,000 reviews)

Families like: Skiing nearby, free breakfast for the whole family

Travelers say...
"Clean . Comfortable for my needs. Staff are friendly and courteous."

Reviewed on May 17, 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.
Hilton Albany
Hilton Garden Inn Albany Airport
Fairfield Inn & Suites by Marriott Albany Downtown
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Need a Car For After Your Flight?

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 – 40 mi from downtown
  • Albany International Airport – 45 mi from downtown
  • HFD – 45 mi 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
Indulge in the feeling of the powdery white snow as you glide down the mountains at Ski Butternut. Need some more options? Don’t miss out on the wonderful natural beauty at Housatonic River Walk. This trail is popular with those wanting a leisurely walk. But there’s more. Indulge your love of the natural world by spending some time at Lake Mansfield Park, a local recreational area.
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.

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.

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.