Cheap Flights to Great Barrington from $38

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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 $83 and $38 for one-way flights to Great Barrington for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Aug 15 - Sat, Aug 23
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$83 Roundtrip, found 2 days ago
$83
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, Aug 15 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sat, Aug 23, priced at $83 found 2 days ago
OriginDestinationTravel DatesFlights From*
MCOWindsor LocksSeptember 5 to September 8$88
TPAWindsor LocksSeptember 8 to September 15$123
ORDWindsor LocksSeptember 18 to September 21$139
MCOLathamSeptember 11 to September 14$143
FLLLathamSeptember 5 to September 9$147
DCAWindsor LocksAugust 25 to August 28$180
DCALathamSeptember 7 to September 9$195
SJUWindsor LocksAugust 14 to September 1$197
SJULathamSeptember 12 to September 15$215
ORDLathamSeptember 2 to September 4$221
TPALathamSeptember 11 to September 15$225
CLTLathamSeptember 20 to September 23$227
ATLLathamSeptember 23 to September 27$237
DENWindsor LocksAugust 16 to August 17$267
LAXLathamOctober 29 to November 3$269
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ORDWindsor LocksAugust 9 to August 11$220
MCOLathamAugust 10 to August 28$225
TPAWindsor LocksAugust 9 to August 11$235
MCOWindsor LocksAugust 9 to August 13$243
ATLWindsor LocksAugust 9 to August 10$245
DCAWindsor LocksAugust 9 to August 13$252
DCALathamAugust 8 to August 13$261
FLLLathamAugust 8 to August 12$307
CLTWindsor LocksAugust 10 to August 21$323
LAXWindsor LocksAugust 9 to August 16$353
SJULathamAugust 8 to August 10$447
LAXLathamAugust 9 to August 26$493
CLTLathamAugust 8 to August 10$505
ATLLathamAugust 8 to August 12$571
DENLathamAugust 9 to August 13$638
*Prices include taxes and fees

Great Barrington Flight Information

Traveling to
Great Barrington
Lowest Price
$83
Number of Airlines Serving
Airlines Serving
Breeze Airways, 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 ...
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

Get rates
Lantern House Motel
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
$86 nightly
The price is $96 total per night from Sep 1 to Sep 2
$96 total
Sep 1 - Sep 2
Total includes taxes and fees
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! (732 reviews)
"It is quiet."

Reviewed on Jul 21, 2025

Monument Mountain Motel
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
$93 nightly
The price is $104 total per night from Sep 2 to Sep 3
$104 total
Sep 2 - Sep 3
Total includes taxes and fees
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 ...
8.2/10 Very Good! (1,004 reviews)
"Close to city center, safe and great costumer experience"

Reviewed on Jul 30, 2025

Quality Inn
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Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
400 Stockbridge Rd, Great Barrington, MA
$75 nightly
The price is $84 total per night from Sep 1 to Sep 2
$84 total
Sep 1 - Sep 2
Total includes taxes and fees
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! (536 reviews)
"The staff was very friendly and the room was clean."

Reviewed on Apr 3, 2025

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 ...
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

Get rates
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
$75 nightly
The price is $84 total per night from Sep 1 to Sep 2
$84 total
Sep 1 - Sep 2
Total includes taxes and fees
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! (536 reviews)
"The staff was very friendly and the room was clean."

Reviewed on Apr 3, 2025

Travelodge by Wyndham Great Barrington Berkshires
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
$86 nightly
The price is $96 total per night from Sep 1 to Sep 2
$96 total
Sep 1 - Sep 2
Total includes taxes and fees
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! (732 reviews)
"It is quiet."

Reviewed on Jul 21, 2025

Monument Mountain Motel
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Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
$93 nightly
The price is $104 total per night from Sep 2 to Sep 3
$104 total
Sep 2 - Sep 3
Total includes taxes and fees
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 ...
8.2/10 Very Good! (1,004 reviews)
"Close to city center, safe and great costumer experience"

Reviewed on Jul 30, 2025

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 ...
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

Get rates
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
$151 nightly
The price is $169 total per night from Aug 27 to Aug 28
$169 total
Aug 27 - Aug 28
Total includes taxes and fees
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 ...
9.2/10 Wonderful! (723 reviews)
"Was the perfect stop over for our way home. All the employees were extremely friendly."

Reviewed on Aug 1, 2025

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
$75 nightly
The price is $84 total per night from Sep 1 to Sep 2
$84 total
Sep 1 - Sep 2
Total includes taxes and fees
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! (536 reviews)
"The staff was very friendly and the room was clean."

Reviewed on Apr 3, 2025

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

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
$93 nightly
The price is $104 total per night from Sep 2 to Sep 3
$104 total
Sep 2 - Sep 3
Total includes taxes and fees
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 ...
8.2/10 Very Good! (1,004 reviews)
"Close to city center, safe and great costumer experience"

Reviewed on Jul 30, 2025

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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 27
found 15 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 27
found 15 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
The Dewey

The Dewey

3.5 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 27
found 15 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Don't see what you're looking for?
See all available trips from Tampa to Great Barrington
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Need a Car For After Your Flight?

Economy

  • 4 people
  • Unlimited mileage
Albany, New York, USA

$50

$100 total
found 2 days ago
Economy undefined

Compact

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$50

$100 total
found 2 days ago
Compact undefined

Midsize

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$58

$116 total
found 6 hours ago
Midsize undefined

Special

  • 4 people
  • Unlimited mileage
Albany, New York, USA

$58

$154 total
found 2 days ago
Special undefined
Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.

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.

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.