Cheap Flights to The Berkshires from $56
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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 $100 and $56 for one-way flights to The Berkshires for the period specified. Prices and availability are subject to change. Additional terms apply
RDU
Raleigh - Durham Intl.
BDL
Bradley Intl.
$112 Roundtrip, found 2 hours ago
$112
Roundtrip
found 2 hours ago
MCO
Orlando Intl.
BDL
Bradley Intl.
$123 Roundtrip, found 23 hours ago
$123
Roundtrip
found 23 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| RSW | Latham | August 29 to September 2 | $100 |
| RSW | Windsor Locks | September 5 to September 13 | $132 |
| JFK | Windsor Locks | September 10 to September 16 | $207 |
| JFK | Latham | July 25 to July 31 | $276 |
| MAN | Windsor Locks | July 16 to August 12 | $1,028 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| RSW | Latham | July 4 to July 11 | $143 |
| RSW | Windsor Locks | July 4 to July 5 | $329 |
| JFK | Windsor Locks | July 4 to July 11 | $361 |
| JFK | Latham | July 3 to July 5 | $796 |
| MAN | Windsor Locks | July 4 to July 8 | $910 |
The Berkshires Flight Information
Traveling to | The Berkshires |
|---|---|
Lowest Price | $100 |
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
42 Stockbridge Rd West Stockbridge MA
$74 nightly
The price is $81 total per night from Jul 7 to Jul 8
$81 total
Jul 7 - Jul 8
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 (1,000 reviews)
"WQW!!!! where do I start!!!!! SHOULD HAVE READ THE REVIEWS, but I thought "everything is nice in the Stockbridge area" WRONG!!!!!! Bad reviews from 10 years ago, so nothing has changed, place is almost falling down. Check-in was through a window, as if you were ordering takeout. An older woman, no ..."
Reviewed on Jun 23, 2026
Wagon Wheel Inn
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
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
Save an average of 15% on thousands of hotels when you're signed in
The Weathervane Motel
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 ...
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
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
26 Glendale Road, RR 183 Stockbridge MA
$358 nightly
The price is $399 total per night from Jul 13 to Jul 14
$399 total
Jul 13 - Jul 14
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 Norman Rockwell Museum and National Shrine ...
9.2/10 Wonderful! (112 reviews)
"Our stay at The Inn was wonderful. Diane and staff could not have been more welcoming or helpful with great suggestions. Shopping and picnic supplies were spot on! Breakfast was delicious and more than plentiful. The pool was not available at this time, but what a beautiful setting. We’ll stay here ..."
Reviewed on Jun 30, 2026
The Orchards Hotel
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 Lower ...
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
Save an average of 15% on thousands of hotels when you're signed in
Wagon Wheel Inn
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
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
276 Brodie Mountain Rd Williamstown MA
$143 nightly
The price is $159 total per night from Jul 6 to Jul 7
$159 total
Jul 6 - Jul 7
Total with taxes and fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,412 reviews)
Families like: Kids pool, playground, game room, skiing nearby
Travelers say...
"Staff was super friendly, splash pad was being renovated so that wasn’t available m.. we had fun but hate that check in is so late and check out so early!"
Reviewed on Jun 30, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$169 nightly
The price is $189 total per night from Jul 1 to Jul 2
$189 total
Jul 1 - Jul 2
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! (1,000 reviews)
"No real breakfast"
Reviewed on Jun 21, 2026
Williamstown Motel
295 Main Street Williamstown MA
$99 nightly
The price is $111 total per night from Jul 5 to Jul 6
$111 total
Jul 5 - Jul 6
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! (329 reviews)
"ok for a night. coffee maker didn't work, ac so so and the breakfast minimal. nearby breakfast joint sucked. will not stay again."
Reviewed on Jun 27, 2026
Save an average of 15% on thousands of hotels when you're signed in
Cozy Corner Motel
284 Sand Springs Rd. Rte 7 Williamstown MA
$93 nightly
The price is $104 total per night from Jul 12 to Jul 13
$104 total
Jul 12 - Jul 13
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 ...
9.2/10 Wonderful! (918 reviews)
Families like: Lazy river, playground, skiing nearby, free breakfast for the whole family
Travelers say...
"Appreciate the clean room and very comfortable beds. The staff was friendly, it's a nice place and a good location to visit local museums and sites."
Reviewed on Jun 30, 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 The Berkshires Flight and Hotel Packages
The Berkshires 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 Atlanta to The Berkshires
View all tripsNeed a Car For After Your Flight?
Midsize
Albany, New York, USA
$62
$331 total
found 1 day ago
Standard
Albany, New York, USA
$63
$334 total
found 1 day ago
Special
Albany, New York, USA
$64
$340 total
found 1 day ago
Fullsize
Albany, New York, USA
$64
$344 total
found 1 day ago
Frequently asked questions
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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