Flights to The Berkshires

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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 $28 for one-way flights to The Berkshires for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
RSWWindsor LocksJan 21 - Jan 24$86
JFKLathamJan 5 - Jan 13$217
JFKWindsor LocksDec 11 - Dec 13$223
RSWLathamJan 30 - Feb 2$223
MANWindsor LocksDec 13 - Dec 31$1,037
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksDec 10 - Dec 11$203
RSWLathamDec 12 - Dec 15$234
RSWWindsor LocksDec 10 - Dec 13$240
JFKLathamDec 12 - Dec 13$421
*Prices include taxes and fees

The Berkshires BDL Flight Information

Traveling to The Berkshires BDL
Lowest Price $84
Number of Airlines Serving 1
Airlines Serving Spirit Airlines, Frontier Airlines, JetBlue Airways, United
Number of Daily Flights 3
Airlines with Direct Flights American Airlines

Flight Review

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
The price is $54 per night from Dec 12 to Dec 12
Situated near the beach, this motel is 2.4 mi (3.8 km) from Berkshire Botanical Garden and within 6 mi (10 km) of Norman Rockwell Museum and National Shrine ...
3/5 (14 reviews)
"This is a cute motel and the staff were pleasant and accommodating."

Reviewed on Aug 15, 2021

Pleasant Valley Motel West Stockbridge
Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
The price is $49 per night from Dec 5 to Dec 5
Located in the heart of Lenox, this motel is within 2 mi (3 km) of Arrowhead Museum, Bousquet Ski Area, and Kennedy Park. Housatonic River and Canoe Meadows ...
3.3/5 (11 reviews)
"The heart shaped jacuzzi"

Reviewed on Jul 25, 2021

Wagon Wheel Inn
Lantern House Motel

Lantern House Motel

2.5 out of 5
256 Stockbridge Road, Great Barrington, MA
The price is $65 per night from Dec 5 to Dec 5
Situated in the mountains, this motel is 0.2 mi (0.4 km) from Housatonic River and 2.5 mi (4 km) from Ski Butternut. Lake Mansfield Park and Mahaiwe Performing ...
4.3/5 Excellent! (20 reviews)
"When I arrived at the hotel I was charged $89.00 instead $70.00 the price that was quoted on your site. That was false advertisement. It made question the site as well as the establishment. I know its not a lot but its the principle."

Reviewed on Jun 2, 2020

Lantern House Motel
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The Weathervane Motel

The Weathervane Motel

2 out of 5
475 South Main St. Route 7, Lanesborough, MA
Situated in Lanesborough, this motel is within 6 mi (10 km) of Berkshire Athenaeum, Berkshire Museum, and Mount Greylock State Reservation Visitor Center. Crane ...
5/5 Exceptional! (2 reviews)
"Nothing fancy but clean and comfortable. Coffee pot didn't work but reception offered to replace it as soon as we reported it. Very handy location for Tanglewood, Edith Wharton's "Mount", and Mount Greylock."

Reviewed on Jul 17, 2019

The 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

Stockbridge Country Inn

Stockbridge Country Inn

4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
Situated in Stockbridge, this luxury bed & breakfast is within 1 mi (2 km) of Housatonic River and Norman Rockwell Museum. National Shrine of the Divine Mercy ...
Stockbridge Country Inn
The Orchards Hotel

The Orchards Hotel

3.5 out of 5
222 Adams Rd, Williamstown, MA
Situated in the mountains, this hotel is within 1 mi (2 km) of Hopkins Observatory, Williams College Museum of Art, and Chapin Library of Rare Books and Manuscripts. ...
3.8/5 Good! (6 reviews)
"There's an old-world elegance to the place. I'd liken it to visiting the home of an elderly, well-off grandmother. A place with faded glory."

Reviewed on Nov 23, 2019

The Orchards Hotel
Federal House Inn

Federal House Inn

3.5 out of 5
1560 Pleasant Street, Route 102, South Lee, MA
Situated in the mountains, this bed & breakfast is 0.2 mi (0.3 km) from Housatonic River and 2.1 mi (3.5 km) from National Shrine of the Divine Mercy. Beartown ...
5/5 Exceptional! (3 reviews)
The Breakfast was World Class
"The atmosphere was friendly, with interesting other guests, good conversations. The best part was the breakfast. It was Imaginative, multi-course, with superb cuisine. My wife was temporarily on a walker and available handicap accessibility was minimal. There was a first floor room which helped a ..."

Reviewed on Dec 17, 2017

Federal House Inn
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Lantern House Motel

Lantern House Motel

2.5 out of 5
256 Stockbridge Road, Great Barrington, MA
Situated in the mountains, this motel is 0.2 mi (0.4 km) from Housatonic River and 2.5 mi (4 km) from Ski Butternut. Lake Mansfield Park and Mahaiwe Performing ...
4.3/5 Excellent! (20 reviews)
"When I arrived at the hotel I was charged $89.00 instead $70.00 the price that was quoted on your site. That was false advertisement. It made question the site as well as the establishment. I know its not a lot but its the principle."

Reviewed on Jun 2, 2020

Lantern House 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.

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, Hancock, MA
The price is $98 per night from Dec 5 to Dec 5
Situated in Hancock, this condo building is 0.1 mi (0.1 km) from Jiminy Peak Mountain Resort and within 6 mi (10 km) of Mount Greylock State Reservation and ...
4/5 Very Good! (34 reviews)
Families like: kids pool, kitchen, game room, skiing nearby
Travelers say...
"Beautiful views. Didn't take advantage of the numerous amenities. Disappointed with the in-room fireplace. Only a light bulb with a faux log setup. Didn't expell any heat, just for ambiance."

Reviewed on Nov 14, 2021

Vacation Village in the Berkshires
Holiday Inn Berkshires, an IHG Hotel
Great for families

Holiday Inn Berkshires, an IHG Hotel

3 out of 5
40 Main St, North Adams, MA
The price is $142 per night from Dec 7 to Dec 7
Located in the heart of North Adams, this hotel is within a 5-minute walk of Western Gateway Heritage State Park and Mass MoCA. North Adams Public Library and ...
3.1/5 (12 reviews)
Families like: indoor pools, game room, skiing nearby, extra beds/cribs
Travelers say...
"Friendly and helpful employees. Quiet rooms. Great location for my visit to MASS MOCA."

Reviewed on Dec 4, 2019

Holiday Inn Berkshires, an IHG Hotel
Stay Berkshires - A Country Inn
Great for families

Stay Berkshires - A Country Inn

2.5 out of 5
1146 Cold Spring Road, Williamstown, MA
The price is $135 per night from Dec 5 to Dec 5
Situated in Williamstown, this hotel is 2.2 mi (3.6 km) from Williamstown Historical Museum and 2.8 mi (4.5 km) from Williams College. Waubeeka Golf Links and ...
4.8/5 Exceptional! (4 reviews)
Families like: outdoor pool, free breakfast for the whole family
Travelers say...
"The inn keepers were so hospitable! They even prepared breakfast 1/2 hour earlier to accommodate us. (10 people) I would add a bathroom rug or mat to cover the very cold floor. We would stay here again!"

Reviewed on Dec 8, 2019

Stay Berkshires - A Country Inn
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Williamstown Motel
Great for families

Williamstown Motel

2 out of 5
295 Main Street, Route 2, Williamstown, MA
The price is $61 per night from Dec 6 to Dec 6
Located in the heart of Williamstown, this motel is within 1 mi (2 km) of Hopkins Observatory, Williams College Museum of Art, and Chapin Library of Rare Books ...
4.1/5 Very Good! (11 reviews)
Families like: skiing nearby, extra beds/cribs, free breakfast for the whole family, laundry
Travelers say...
"Welcoming hosts!"

Reviewed on Oct 7, 2021

Williamstown 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.

Need a Car For After Your Flight?

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.