Cheap Flights to The Berkshires from $49

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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 $84 and $49 for one-way flights to The Berkshires for the period specified. Prices and availability are subject to change. Additional terms apply

Mon, Oct 26 - Mon, Nov 2
PIE
St. Petersburg-Clearwater Intl.
ALB
Albany Intl.
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Mon, Oct 26 from St. Petersburg-Clearwater Intl. to Albany Intl., returning Mon, Nov 2, priced at $84 found 2 days ago
Thu, Sep 17 - Mon, Sep 21
MCO
Orlando Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 17 hours ago
$98
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Sep 17 from Orlando Intl. to Bradley Intl., returning Mon, Sep 21, priced at $98 found 17 hours ago
OriginDestinationTravel DatesFlights From*
RSWLathamOctober 10 to October 17$142
RSWWindsor LocksSeptember 29 to October 20$174
JFKWindsor LocksOctober 24 to October 27$227
JFKLathamSeptember 18 to September 20$273
MANWindsor LocksSeptember 24 to September 28$1,023
MANLathamAugust 28 to August 30$1,551
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWLathamAugust 15 to August 21$240
JFKWindsor LocksAugust 16 to August 18$311
RSWWindsor LocksAugust 16 to August 23$365
JFKLathamAugust 15 to August 20$426
MANWindsor LocksAugust 16 to August 29$1,283
*Prices include taxes and fees

The Berkshires Flight Information

Traveling to
The Berkshires
Lowest Price
$84
Number of Airlines Serving
Airlines Serving
Frontier Airlines, Allegiant Air
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
$69 nightly
The price is $76 total per night from Aug 11 to Aug 12
$76 total
Aug 11 - Aug 12
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 ...
6.8/10 (1,004 reviews)
"La paix du lieu"

Reviewed on Aug 7, 2026

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

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd Lenox MA
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! (641 reviews)
"We've been in worse, but not by much. It kept the wind out of our hair and the shower had plenty of hot water. That's about it"

Reviewed on Oct 26, 2025

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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 ...
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

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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 Pontoosuc Lake are located ...
7.2/10 Good! (128 reviews)
"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
$358 nightly
The price is $399 total per night from Aug 24 to Aug 25
$399 total
Aug 24 - Aug 25
Total with taxes and fees
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
9.2/10 Wonderful! (114 reviews)
"Very lovely beautiful Room and property The outside pool was not available"

Reviewed on Jul 30, 2026

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 Massachusetts Museum of Contemporary ...
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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 ...
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

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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 Lenox MA
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! (641 reviews)
"We've been in worse, but not by much. It kept the wind out of our hair and the shower had plenty of hot water. That's about it"

Reviewed on Oct 26, 2025

Get rates
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
$128 nightly
The price is $143 total per night from Aug 31 to Sep 1
$143 total
Aug 31 - Sep 1
Total with taxes and fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
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
$139 nightly
The price is $155 total per night from Sep 7 to Sep 8
$155 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,003 reviews)
"Room was clean and staff was nice. Air conditioner was a little noisy"

Reviewed on Aug 1, 2026

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Williamstown Motel

Williamstown Motel

2 out of 5
295 Main Street Williamstown MA
$96 nightly
The price is $107 total per night from Aug 16 to Aug 17
$107 total
Aug 16 - Aug 17
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! (335 reviews)
"The host gave us a free upgrade. He helped us find a good place for dinner. He couldn’t have been more helpful! Breakfast choices were good quality. Rooms were quiet."

Reviewed on Jul 25, 2026

Opens in a new windowWilliamstown Motel
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Cozy Corner Motel
Great for families

Cozy Corner Motel

2 out of 5
284 Sand Springs Rd. Rte 7 Williamstown MA
$100 nightly
The price is $111 total per night from Aug 9 to Aug 10
$111 total
Aug 9 - Aug 10
Total with taxes and fees
Book a stay at this family-friendly motel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Opens in a new windowCozy Corner 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.
Four Points by Sheraton Albany

Four Points by Sheraton Albany

3 out of 5
Price was $860, price is now $757 per person
$757
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Price was $1,251, price is now $1,077 per person
$1,077
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
Price was $986, price is now $866 per person
$866
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
Don't see what you're looking for?
See all available trips from Denver to The Berkshires
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Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

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 $84. 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 $84. 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 $84 and $1,551 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!

 

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*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.