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Great Barrington

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Great Barrington Flights as Low as $141

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Tue, May 20 - Tue, May 27
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$141 Roundtrip, found 21 hours ago
$141
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Tue, May 20 from Southwest Florida Intl. to Bradley Intl., returning Tue, May 27, priced at $141 found 21 hours ago
JetBlue Airways
Wed, May 21 - Tue, May 27
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$144 Roundtrip, found 21 hours ago
$144
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Wed, May 21 from Southwest Florida Intl. to Bradley Intl., returning Tue, May 27, priced at $144 found 21 hours ago
American Airlines
Tue, Aug 5 - Tue, Aug 12
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$145 Roundtrip, found 12 hours ago
$145
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Aug 5 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Aug 12, priced at $145 found 12 hours ago
JetBlue Airways
Tue, May 20 - Wed, May 21
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 21 hours ago
$161
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Tue, May 20 from Southwest Florida Intl. to Bradley Intl., returning Wed, May 21, priced at $161 found 21 hours ago
Breeze Airways
Wed, Jul 30 - Sun, Aug 3
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$162 Roundtrip, found 13 hours ago
$162
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Wed, Jul 30 from Southwest Florida Intl. to Bradley Intl., returning Sun, Aug 3, priced at $162 found 13 hours ago
JetBlue Airways
Thu, May 22 - Sat, May 24
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$164 Roundtrip, found 21 hours ago
$164
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Thu, May 22 from Southwest Florida Intl. to Bradley Intl., returning Sat, May 24, priced at $164 found 21 hours ago
American Airlines
Tue, Aug 5 - Tue, Aug 12
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$165 Roundtrip, found 12 hours ago
$165
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Aug 5 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Aug 12, priced at $165 found 12 hours ago
Frontier Airlines
Sat, May 31 - Sat, Jun 7
BWI
Baltimore Washington Intl. Thurgood Marshall
BDL
Bradley Intl.
$172 Roundtrip, found 19 hours ago
$172
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Baltimore Washington Intl. Thurgood Marshall to Bradley Intl., returning Sat, Jun 7, priced at $172 found 19 hours ago
Breeze Airways
Fri, May 23 - Sun, May 25
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$176 Roundtrip, found 21 hours ago
$176
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Fri, May 23 from Southwest Florida Intl. to Bradley Intl., returning Sun, May 25, priced at $176 found 21 hours ago
Spirit Airlines
Wed, Jul 30 - Sun, Aug 3
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$182 Roundtrip, found 13 hours ago
$182
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Wed, Jul 30 from Southwest Florida Intl. to Bradley Intl., returning Sun, Aug 3, priced at $182 found 13 hours ago
Bargain Flight
Sat, May 17 - Wed, May 28
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$187 Roundtrip, found 15 hours ago
$187
Roundtrip
found 15 hours ago
Select Bargain Flight flight, departing Sat, May 17 from Charlotte-Douglas Intl. to Bradley Intl., returning Wed, May 28, priced at $187 found 15 hours ago
Delta
Sat, Aug 2 - Tue, Aug 12
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 12 hours ago
$197
Roundtrip
found 12 hours ago
Select Delta flight, departing Sat, Aug 2 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Aug 12, priced at $197 found 12 hours ago
Spirit Airlines
Sat, May 31 - Sun, Jun 8
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$214 Roundtrip, found 5 days ago
$214
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, May 31 from Luis Munoz Marin Intl. to Bradley Intl., returning Sun, Jun 8, priced at $214 found 5 days ago
American Airlines
Fri, Sep 12 - Tue, Sep 16
BWI
Baltimore Washington Intl. Thurgood Marshall
ALB
Albany Intl.
$271 Roundtrip, found 2 days ago
$271
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Sep 12 from Baltimore Washington Intl. Thurgood Marshall to Albany Intl., returning Tue, Sep 16, priced at $271 found 2 days ago
Bargain Flight
Tue, Aug 26 - Thu, Aug 28
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$283 Roundtrip, found 6 days ago
$283
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Tue, Aug 26 from Charlotte-Douglas Intl. to Albany Intl., returning Thu, Aug 28, priced at $283 found 6 days ago
Delta
Tue, Jul 8 - Tue, Jul 15
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 8 from Southwest Florida Intl. to Albany Intl., returning Tue, Jul 15, priced at $285 found 1 day ago

Cheap Flights to Great Barrington

Fall in love at first flight with your vacation to Great Barrington by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Great Barrington on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Great Barrington, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Great Barrington

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Great Barrington with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the ALB airport.

What is the cheapest month to fly to Great Barrington?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Great Barrington are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Great Barrington?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 14 to choose from for your flight to Great Barrington.

What airport is best to fly into Great Barrington?

When you’re planning your trip to Great Barrington, convenience is the name of the game. Luckily, Great Barrington Pittsfield Municipal Airport is nearby so you can deplane and get going on checking off everything on your Great Barrington must-do list.

How much are flights to Great Barrington?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Great Barrington on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $141, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Great Barrington?

The trick to saving a stack of cash on your flight to Great Barrington? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $141 right now, why wait?

Great Barrington Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$96

Last Minute Hotel Deals in Great Barrington

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 14 to May 15
$85
includes taxes & fees
May 14 - May 15
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! (1,002 reviews)
"Room was fine stayed 1 night good coffee and breakfast in the lobby till 10"

Reviewed on Apr 26, 2025

Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
The price is $139 per night from May 11 to May 12
$139
includes taxes & fees
May 11 - May 12
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 ...
8.8/10 Excellent! (613 reviews)
Perfect hotel Berkshires stay
"The rooms were clean and comfortable and spacious. The breakfast was expansive given the small size of the hotel and was a great thing for our daughter. Met with business people there and had a great time in the pool!"

Reviewed on Apr 28, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 $169 per night from May 26 to May 27
$169
includes taxes & fees
May 26 - May 27
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! (697 reviews)
"Nice property right in town. Close to shops and restaurants"

Reviewed on Apr 28, 2025

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Little Lion
The Little Lion
3 out of 5
506 Stockbridge Road, Great Barrington, MA
The price is $85 per night from May 14 to May 15
$85
includes taxes & fees
May 14 - May 15
Stay at this 3-star motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (482 reviews)
"I had a great time at this motel. It was close to hiking trails that I was doing. It was extremely dog friendly. A lastly, it was a close drive to all the good shopping and in town."

Reviewed on Apr 25, 2025

The Little Lion
Monument Mountain Motel
Monument Mountain Motel
2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
The price is $89 per night from May 1 to May 2
$89
includes taxes & fees
May 1 - May 2
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 ...
"Good for a night or maybe two. Fridge realy needed to be cleaned but all else seemed good. Staff very friendly"

Reviewed on Apr 27, 2025

Monument Mountain 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 $84 per night from May 1 to May 2
$84
includes taxes & fees
May 1 - May 2
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! (523 reviews)
"The staff was very friendly and the room was clean."

Reviewed on Apr 3, 2025

Travelodge by Wyndham Great Barrington Berkshires
East Rock Inn
East Rock Inn
2 out of 5
304 State Rd, Great Barrington, MA
The price is $176 per night from May 1 to May 2
$176
includes taxes & fees
May 1 - May 2
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Popular attractions Housatonic River and Housatonic River Walk are located ...
9.4/10 Exceptional! (24 reviews)
"The property is well maintained and set back from the road. It was very quiet and the rooms are fantastic. A must stay if you are going to be in the area."

Reviewed on Mar 4, 2025

East Rock Inn
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $115 per night from May 1 to May 2
$115
includes taxes & fees
May 1 - May 2
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (570 reviews)
"Loved the entire vibe of the property. Decor, ease of check in / out."

Reviewed on Apr 27, 2025

Life House Berkshires
See all 1,483 properties in Great 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.