Cheap Flights to Great Barrington from $29
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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 $58 and $29 for one-way flights to Great Barrington for the period specified. Prices and availability are subject to change. Additional terms apply
MCO
Orlando Intl.
BDL
Bradley Intl.
$58 Roundtrip, found 2 hours ago
$58
Roundtrip
found 2 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MCO | Windsor Locks | January 9 to January 12 | $58 |
| FLL | Latham | February 14 to February 23 | $135 |
| FLL | Windsor Locks | February 12 to February 21 | $141 |
| SJU | Windsor Locks | January 12 to January 19 | $146 |
| DEN | Windsor Locks | February 10 to February 25 | $158 |
| DCA | Windsor Locks | March 12 to March 14 | $189 |
| CLT | Windsor Locks | February 23 to February 27 | $197 |
| CLT | Latham | January 24 to February 10 | $199 |
| DCA | Latham | January 13 to January 24 | $209 |
| LAX | Windsor Locks | March 25 to April 9 | $228 |
| ORD | Latham | February 18 to February 18 | $248 |
| SJU | Latham | January 13 to January 18 | $251 |
| TPA | Latham | January 14 to January 17 | $284 |
| LAX | Latham | January 13 to January 17 | $339 |
| ATL | Latham | January 28 to February 11 | $339 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| SJU | Windsor Locks | December 27 to January 5 | $173 |
| MCO | Windsor Locks | December 28 to January 7 | $186 |
| FLL | Windsor Locks | December 27 to December 31 | $281 |
| MCO | Latham | December 27 to January 9 | $293 |
| DCA | Latham | December 27 to January 8 | $306 |
| DCA | Windsor Locks | December 27 to January 6 | $322 |
| DEN | Windsor Locks | December 28 to January 4 | $337 |
| CLT | Latham | December 27 to January 1 | $371 |
| TPA | Windsor Locks | December 27 to December 31 | $375 |
| ORD | Windsor Locks | December 27 to January 1 | $453 |
| LAX | Windsor Locks | December 28 to January 2 | $484 |
| TPA | Latham | December 28 to December 28 | $538 |
| DEN | Latham | December 27 to December 29 | $552 |
| ATL | Latham | December 27 to December 28 | $699 |
| LAX | Latham | December 27 to January 1 | $755 |
Great Barrington Flight Information
Traveling to | Great Barrington |
|---|---|
Lowest Price | $58 |
Number of Airlines Serving | |
Airlines Serving | Frontier 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
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
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
$67 nightly
The price is $74 total per night from Jan 1 to Jan 2
$74 total
Jan 1 - Jan 2, 2026
Total with 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! (807 reviews)
Yes clean room, staff was grea Frig. Microwave but no coffee. Maker
Reviewed on Dec 21, 2025
Quality Inn
372 Main Street Great Barrington MA
$76 nightly
The price is $85 total per night from Jan 7 to Jan 8
$85 total
Jan 7 - Jan 8, 2026
Total with 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 ...
8.4/10 Very Good! (1,000 reviews)
My go to place for my ski weekends
Reviewed on Dec 20, 2025
Save an average of 15% on thousands of hotels when you're signed in
Travelodge by Wyndham Great Barrington Berkshires
400 Stockbridge Rd Great Barrington MA
$75 nightly
The price is $84 total per night from Dec 28 to Dec 29
$84 total
Dec 28 - Dec 29
Total with 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! (562 reviews)
Very nice people at the desk, room was very nice
Reviewed on Nov 22, 2025
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
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
Travelodge by Wyndham Great Barrington Berkshires
400 Stockbridge Rd Great Barrington MA
$75 nightly
The price is $84 total per night from Dec 28 to Dec 29
$84 total
Dec 28 - Dec 29
Total with 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! (562 reviews)
Very nice people at the desk, room was very nice
Reviewed on Nov 22, 2025
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
$67 nightly
The price is $74 total per night from Jan 1 to Jan 2
$74 total
Jan 1 - Jan 2, 2026
Total with 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! (807 reviews)
Yes clean room, staff was grea Frig. Microwave but no coffee. Maker
Reviewed on Dec 21, 2025
Save an average of 15% on thousands of hotels when you're signed in
Quality Inn
372 Main Street Great Barrington MA
$76 nightly
The price is $85 total per night from Jan 7 to Jan 8
$85 total
Jan 7 - Jan 8, 2026
Total with 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 ...
8.4/10 Very Good! (1,000 reviews)
My go to place for my ski weekends
Reviewed on Dec 20, 2025
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
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
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd Great Barrington MA
$135 nightly
The price is $151 total per night from Jan 11 to Jan 12
$151 total
Jan 11 - Jan 12, 2026
Total with 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! (758 reviews)
Yes
Reviewed on Nov 21, 2025
Travelodge by Wyndham Great Barrington Berkshires
400 Stockbridge Rd Great Barrington MA
$75 nightly
The price is $84 total per night from Dec 28 to Dec 29
$84 total
Dec 28 - Dec 29
Total with 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! (562 reviews)
Very nice people at the desk, room was very nice
Reviewed on Nov 22, 2025
Save an average of 15% on thousands of hotels when you're signed in
Quality Inn
372 Main Street Great Barrington MA
$76 nightly
The price is $85 total per night from Jan 7 to Jan 8
$85 total
Jan 7 - Jan 8, 2026
Total with 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 ...
8.4/10 Very Good! (1,000 reviews)
My go to place for my ski weekends
Reviewed on Dec 20, 2025
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 - first class flights
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Greenville to Great Barrington
View all tripsNeed a Car For After Your Flight?
Economy
Albany, New York, USA
$50
$133 total
found 3 days ago
Compact
Albany, New York, USA
$51
$136 total
found 3 days ago
Midsize
Albany, New York, USA
$52
$139 total
found 3 days ago
Special
Albany, New York, USA
$54
$144 total
found 3 days ago
Lowest prices found within the past 3 days. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
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!
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