Cheap Flights to The Berkshires from $51

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How Much Does it Cost To Fly To The Berkshires?

The cheapest prices found with in the last 7 days for return flights were $97 and $51 for one-way flights to The Berkshires for the period specified. Prices and availability are subject to change. Additional terms apply

Sat, Oct 11 - Mon, Oct 20
MCO
Orlando Intl.
BDL
Bradley Intl.
$99 Roundtrip, found 5 days ago
$99
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Oct 11 from Orlando Intl. to Bradley Intl., returning Mon, Oct 20, priced at $99 found 5 days ago
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksOctober 2 to October 6$97
RSWLathamNovember 4 to November 11$122
RSWWindsor LocksNovember 6 to November 9$143
JFKLathamOctober 14 to October 21$238
MANWindsor LocksOctober 1 to October 9$719
MANLathamNovember 13 to November 27$822
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksSeptember 27 to September 29$97
RSWWindsor LocksSeptember 28 to September 30$261
JFKLathamSeptember 27 to October 15$327
RSWLathamSeptember 27 to October 7$469
*Prices include taxes and fees

The Berkshires Flight Information

Traveling to
The Berkshires
Lowest Price
$97
Number of Airlines Serving
Airlines Serving
Breeze Airways
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing The Berkshires Accommodation Deals

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
$66 nightly
The price is $73 total per night from Sep 28 to Sep 29
$73 total
Sep 28 - Sep 29
Total with taxes and fees
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.6/10 (1,002 reviews)
"Very nice staff!!"

Reviewed on Aug 29, 2025

Opens in a new windowPleasant Valley Motel West Stockbridge
Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
$69 nightly
The price is $77 total per night from Sep 22 to Sep 23
$77 total
Sep 22 - Sep 23
Total with taxes and fees
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...
7/10 Good! (626 reviews)
"And I mean the David Lynch as a compliment."

Reviewed on Aug 14, 2025

Opens in a new windowWagon Wheel Inn
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

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Opens in a new windowLantern House Motel
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The Weathervane Motel

The Weathervane Motel

2 out of 5
475 South Main St. Route 7, Lanesborough, MA
Stay at this motel in Lanesborough. Enjoy free WiFi, free parking, and a garden. Popular attractions Jiminy Peak Mountain Resort and Crane Museum of Papermaking ...
"Booked a king bed but when I got there they told me no cable in that room. They gave me a room with a double bed that were on top of being small were very uncomfortable plus so much dust in air conditioner my allergies were affected plus it stunk couldn’t stay had to repack and go drive around and ..."

Reviewed on Oct 1, 2020

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Opens in a new windowThe Weathervane Motel
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 The Berkshires

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
$335 nightly
The price is $374 total per night from Oct 6 to Oct 7
$374 total
Oct 6 - Oct 7
Total with taxes and fees
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
"Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly."

Reviewed on Nov 2, 2024

Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Orchards Hotel

The Orchards Hotel

2.5 out of 5
222 Adams Rd, Williamstown, MA
Book a stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Colonial Plaza and Linear ...
"A little dated. Restaurant shut down for renovations, disappointing"

Reviewed on Mar 9, 2020

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Opens in a new windowThe Orchards Hotel
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

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Opens in a new windowLantern House Motel
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Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
$69 nightly
The price is $77 total per night from Sep 22 to Sep 23
$77 total
Sep 22 - Sep 23
Total with taxes and fees
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...
7/10 Good! (626 reviews)
"And I mean the David Lynch as a compliment."

Reviewed on Aug 14, 2025

Opens in a new windowWagon Wheel 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 The Berkshires

Vacation Village in the Berkshires
Great for families

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
$79 nightly
The price is $88 total per night from Sep 24 to Sep 25
$88 total
Sep 24 - Sep 25
Total with taxes and fees
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,004 reviews)

Families like: Kids pool, playground, game room, skiing nearby

Travelers say...
"Quiet, clean, beautifully landscaped- such a comfy bed!"

Reviewed on Sep 13, 2025

Opens in a new windowVacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
$152 nightly
The price is $170 total per night from Sep 24 to Sep 25
$170 total
Sep 24 - Sep 25
Total with taxes and fees
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,006 reviews)
"No food, no parking near…"

Reviewed on Sep 19, 2025

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Stay Berkshires

Stay Berkshires

2 out of 5
1146 Cold Spring Road, Williamstown, MA
Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Margaret Lindley Park and Lindley Park are located ...
8.2/10 Very Good! (353 reviews)
"Nice option to stay near MASS MOCA."

Reviewed on Dec 4, 2024

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Opens in a new windowStay Berkshires
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Williamstown Motel

Williamstown Motel

2 out of 5
295 Main Street, Route 2, Williamstown, MA
$88 nightly
The price is $99 total per night from Sep 22 to Sep 23
$99 total
Sep 22 - Sep 23
Total with taxes and fees
Book a stay at this business-friendly motel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (296 reviews)
"The owner was so nice. She shuttled me and amother hiker back to the Appalachian trailhead after breakfast. The room was clean. Basic motel. Organic grocery across the street. Mexican restaurant nearby."

Reviewed on Sep 16, 2025

Opens in a new windowWilliamstown Motel
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 The Berkshires Flight and Hotel Packages

The Berkshires flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $683, price is now $503 per person
$503
per person
Oct 31 - Nov 3
found 5 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $878, price is now $538 per person
$538
per person
Oct 31 - Nov 3
found 5 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

3 out of 5
Save 100% on your flight
Price was $5,219, price is now $3,926 per person
$3,926
per person
Oct 31 - Nov 3
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
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Need a Car For After Your Flight?

Standard

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

$60

$160 total
found 5 days ago
Standard undefined

Compact

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

$61

$163 total
found 5 days ago
Compact undefined

Special

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

$61

$163 total
found 5 days ago
Special undefined

Economy Special

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

$64

$128 total
found 5 days ago
Economy Special undefined
Lowest prices found within the past 5 days. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to The Berkshires?
The next vacation you take doesn't have to make a huge dent in your finances. During the last seven days, the cheapest roundtrip flight to The Berkshires cost $97. Find a cheap fare and spend the cash you save on cool experiences. This price was available on Travelocity for flights to The Berkshires departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to The Berkshires?
If you've been daydreaming about a getaway in The Berkshires, October is the cheapest month to hop on a plane. This is based on Travelocity's direct return flight demand between January and December last year. Work out your ideal dates and lock in your flights today.
How can I check my flight status to The Berkshires?
Check for updates on your flight to The Berkshires, make changes to your journey and loads more from our useful Trips portal. Located at the top of the Travelocity homepage, it's your one-stop shop for viewing and managing your bookings. Just log in or create a new account in seconds. Savvy adventurers will also enjoy the Travelocity app. You'll get real-time travel updates, as well as the ability to view deals on hotels, rental cars and activities while you're out and about. If you have friends or family flying with you, it's also a convenient way to share your flight details with each other.
How do I find the best deals on flights to The Berkshires?
Be flexible with your travel dates and there's a good chance you'll find a sensational deal. When searching for flights on Travelocity, click the "Flexible dates" box above your results to compare prices with nearby days. Also try to book in advance and avoid vacation periods. In the last seven days, the best price for a roundtrip flight to The Berkshires was $97. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to The Berkshires with Travelocity?
Check out cheap flights to The Berkshires with Travelocity and begin packing for your next adventure. With round-the-clock customer support during every stage of your trip and our Price Match Guarantee, we take the hassle out of reserving cheap family flights, hotels, rental cars and more. Snag an awesome deal today and prepare for the adventure of a lifetime.
What are the most popular flight routes to The Berkshires?
Whether you're thinking about a short trip or a long escape, we can help you book your ideal flight to The Berkshires. Major flight routes to this destination include:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 1,131 flights a month.
  • Chicago, IL (ORD-O'Hare Intl.) to Bradley Intl. Airport (BDL) - 1,048 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 866 flights a month.

How much is a flight to The Berkshires on average?
Airfares for roundtrip flights to The Berkshires were priced between $97 and $822 in the last seven days. The moment you see a great deal, lock it in and get ready to embark on the getaway of your dreams with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to The Berkshires?
Below are a handful of major direct flights to The Berkshires with their average journey times:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 15 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 9 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 1 hour and 12 minutes

What can I expect on a flight to The Berkshires?
This will mostly depend on your departure point and which air carrier you're traveling with. You're likely to find all types of flights to The Berkshires, from first class fares to cheap flights for family vacations. If a flight is classed as long haul, the airline will usually provide hot meals and entertainment as well as games for the kids.

Flights To The Berkshires

The Berkshires has a legendary draw for travelers who like their vacations quaint and quiet. Nestled between Massachusetts's Taconic Mountains and the Hudson Highlands, it is the perfect place for people who want to escape the hectic pace of city life. It's a largely rural area with seemingly endless options for outdoor recreation, and plenty of small towns that offer a lot of unique and delicious options for dining. When you fly to The Berkshires, you'll notice the slower pace of life here right away—a pace that has a rejuvenating effect on the minds and bodies of all visitors.

Transportation from PSF

The Berkshires flights land at Pittsfield Municipal Airport (PSF) in Berkshire County. Considering that this is a largely rural area, there aren't many public transportation options. You can call for a taxi while you find your luggage, or you can get a car at one of several nearby rental agencies. Some local hotels offer shuttle service to and from the airport for their guests; you can contact hotels in The Berkshires to see which ones offer this option. After you get settled in at your hotel, you may want to visit a restaurant for some nourishment. Thankfully., there are plenty of excellent places to dine in Monterey and New Marlborough. You may choose an option that's near your hotel—that way, you can start your vacation with a relaxing, no-fuss meal.

Enjoy the Culture and Beauty of The Berkshires

When you choose The Berkshires as your next vacation destination, you'll have seemingly endless fun activities to consider. There are wonderful art museums in Stockbridge, North Adams, and Williamstown. If you like wandering through nature, you can visit any of the beautiful local parks and stunning preserves. By booking vacations in The Berkshires here at Travelocity, you can save up to $537, leaving you with plenty of money to enjoy any activity in The Berkshires that catches your attention. Make your travel plans 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.