Cheap Flights to Great Barrington from $61
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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 $129 and $61 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.
$129 Roundtrip, found 1 day ago
$129
Roundtrip
found 1 day ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MCO | Windsor Locks | August 26 to August 31 | $134 |
| TPA | Windsor Locks | September 26 to October 4 | $142 |
| DCA | Windsor Locks | July 22 to July 29 | $167 |
| FLL | Latham | August 24 to August 27 | $167 |
| MCO | Latham | August 12 to August 15 | $187 |
| ATL | Windsor Locks | August 22 to August 29 | $193 |
| ORD | Windsor Locks | September 5 to September 11 | $201 |
| DCA | Latham | September 29 to October 3 | $242 |
| SJU | Windsor Locks | August 28 to August 31 | $253 |
| ORD | Latham | September 1 to September 8 | $269 |
| CLT | Windsor Locks | July 18 to July 20 | $274 |
| ATL | Latham | August 1 to August 25 | $291 |
| LAX | Latham | August 27 to August 29 | $324 |
| CLT | Latham | August 19 to August 22 | $339 |
| SJU | Latham | August 11 to August 18 | $406 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MCO | Windsor Locks | July 4 to July 18 | $211 |
| FLL | Windsor Locks | July 4 to July 8 | $231 |
| TPA | Windsor Locks | July 4 to July 22 | $265 |
| MCO | Latham | July 3 to July 23 | $333 |
| ORD | Windsor Locks | July 4 to July 17 | $343 |
| DCA | Windsor Locks | July 3 to July 6 | $347 |
| SJU | Windsor Locks | July 3 to July 6 | $359 |
| ATL | Windsor Locks | July 3 to July 6 | $368 |
| LAX | Windsor Locks | July 4 to July 24 | $390 |
| TPA | Latham | July 5 to July 9 | $483 |
| DEN | Latham | July 3 to July 5 | $509 |
| SJU | Latham | July 4 to July 11 | $542 |
| CLT | Latham | July 3 to July 5 | $543 |
| LAX | Latham | July 5 to July 7 | $710 |
| ATL | Latham | July 5 to July 9 | $785 |
Great Barrington Flight Information
Traveling to | Great Barrington |
|---|---|
Lowest Price | $129 |
Number of Airlines Serving | |
Airlines Serving | Breeze Airways, 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 National Shrine of the Divine Mercy and Housatonic ...
8.2/10 Very Good! (455 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
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
$124 nightly
The price is $138 total per night from Jun 29 to Jun 30
$138 total
Jun 29 - Jun 30
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 ...
9/10 Wonderful! (874 reviews)
"The owners are very pleasant The room was very clean The shower was very hot The AC was very cold"
Reviewed on Jun 15, 2026
Quality Inn Great Barrington
372 Main Street Great Barrington MA
$118 nightly
The price is $132 total per night from Jul 16 to Jul 17
$132 total
Jul 16 - Jul 17
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 ...
8.6/10 Excellent! (1,001 reviews)
"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain ..."
Reviewed on Jun 22, 2026
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
$89 nightly
The price is $99 total per night from Jun 29 to Jun 30
$99 total
Jun 29 - Jun 30
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. ...
7.6/10 Good! (587 reviews)
"This is a quiet, no frills place. It’s hard to find a reasonably priced motel in the Berkshires in-season and this is it. Fancy it is not. Stylish, also no. But it was clean and the mattresses were comfortable."
Reviewed on Jun 22, 2026
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 National Shrine of the Divine Mercy and Housatonic ...
8.2/10 Very Good! (455 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
Travelodge by Wyndham Great Barrington Berkshires
400 Stockbridge Rd Great Barrington MA
$89 nightly
The price is $99 total per night from Jun 29 to Jun 30
$99 total
Jun 29 - Jun 30
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. ...
7.6/10 Good! (587 reviews)
"This is a quiet, no frills place. It’s hard to find a reasonably priced motel in the Berkshires in-season and this is it. Fancy it is not. Stylish, also no. But it was clean and the mattresses were comfortable."
Reviewed on Jun 22, 2026
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
$124 nightly
The price is $138 total per night from Jun 29 to Jun 30
$138 total
Jun 29 - Jun 30
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 ...
9/10 Wonderful! (874 reviews)
"The owners are very pleasant The room was very clean The shower was very hot The AC was very cold"
Reviewed on Jun 15, 2026
Save an average of 15% on thousands of hotels when you're signed in
Quality Inn Great Barrington
372 Main Street Great Barrington MA
$118 nightly
The price is $132 total per night from Jul 16 to Jul 17
$132 total
Jul 16 - Jul 17
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 ...
8.6/10 Excellent! (1,001 reviews)
"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain ..."
Reviewed on Jun 22, 2026
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 National Shrine of the Divine Mercy and Housatonic ...
8.2/10 Very Good! (455 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
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd Great Barrington MA
$186 nightly
The price is $208 total per night from Jun 30 to Jul 1
$208 total
Jun 30 - Jul 1
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 ...
9.4/10 Exceptional! (788 reviews)
"Dawn was super helpful in getting us checked in."
Reviewed on Jun 14, 2026
Travelodge by Wyndham Great Barrington Berkshires
400 Stockbridge Rd Great Barrington MA
$89 nightly
The price is $99 total per night from Jun 29 to Jun 30
$99 total
Jun 29 - Jun 30
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. ...
7.6/10 Good! (587 reviews)
"This is a quiet, no frills place. It’s hard to find a reasonably priced motel in the Berkshires in-season and this is it. Fancy it is not. Stylish, also no. But it was clean and the mattresses were comfortable."
Reviewed on Jun 22, 2026
Save an average of 15% on thousands of hotels when you're signed in
Quality Inn Great Barrington
372 Main Street Great Barrington MA
$118 nightly
The price is $132 total per night from Jul 16 to Jul 17
$132 total
Jul 16 - Jul 17
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 ...
8.6/10 Excellent! (1,001 reviews)
"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain ..."
Reviewed on Jun 22, 2026
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.
Don't see what you're looking for?
See all available trips from New York to Great Barrington
View all tripsNeed a Car For After Your Flight?
Economy
PITTSFIELD, USA
$86
$201 total
found 15 hours ago
Special
PITTSFIELD, USA
$86
$201 total
found 15 hours ago
Compact
Pittsfield, Massachusetts, USA
$86
$201 total
found 15 hours ago
Midsize
PITTSFIELD, USA
$87
$205 total
found 15 hours ago
Lowest prices found within the past 15 hours. 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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