Berkshire County Vacations & Trips from $731
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Your Berkshire County Vacation
With a Berkshire County vacation package, you can forget about the stress of planning and simply focus on experiencing what this exciting destination has on offer. Kick off your trip to Berkshire County with a few nights in Lenox visiting popular attractions like National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown is another city that draws crowds from far and wide. Massachusetts Museum of Contemporary Art and Mount Greylock are two of the leading places to see in this destination. If you're ready to stop daydreaming and start doing, Expedia will help turn your Berkshire County vacation into reality.
Top destinations in Berkshire County
Lee
Adams
North Adams
Lenox
Williamstown
Great Barrington
Pittsfield
Stockbridge
Hancock
The Latest Berkshire County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Old Catskill Game Farm Inn
$2,686
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.8/10 Exceptional! (36 reviews)
Everything was amazing. Shawn was awesome. He greeted you when we came in. It's definitely experiences. All I can say we had a great time. A little quirky.Amazing history set on 200 acres closed down zoo
Reviewed on Sep 21, 2026
Find the Best Berkshire County Vacation Packages
Berkshire County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Top Sights | Bash Bish Falls State Park, Pittsfield State Forest and Tolland State Forest |
Berkshire County Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (2,796 reviews)
"Everything was absolutely perfect! Staff was extremely friendly and the property is so clean and inviting. We loved it so much that we extended our stay!"
Reviewed on Oct 25, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$115 nightly
$128 total
Nov 24 - Nov 25
Total with taxes and fees
9/10 Wonderful! (1,230 reviews)
"We loved our experience here. The rooms were better than we could have imagined. Having a full kitchen and separate bedroom on vacation is beyond brilliant. The pool was pretty awesome - sunset looks pretty great through the back windows. They show a movie in the common room on their big TV every ..."
Reviewed on Oct 26, 2026
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
$75 nightly
$84 total
Nov 22 - Nov 23
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
"We love staying at this hotel every fall. It is in an easy access location with plenty of parking and very clean. The staff are very friendly and the breakfast is fantastic. We’ll be back!!"
Reviewed on Oct 26, 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.
Stay near popular Berkshire County attractions
Jiminy Peak Mountain Resort
8.8/10 (311 reviews)
Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this family-friendly area.
Tanglewood Music Center
9.6/10 (457 reviews)
You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.
Williams College
9.4/10 (534 reviews)
Take a campus tour or just explore the area of Williams College, during your travels in Williamstown. In the area, take in the fascinating museums and mountain views.
Photo by Adnan Kakazai
Norman Rockwell Museum
9.4/10 (347 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
Photo by Caminante
Massachusetts Museum of Contemporary Art
9.4/10 (246 reviews)
You can spend time browsing the exhibits at Massachusetts Museum of Contemporary Art in North Adams. Take in the fascinating museums while you're in the area.
Ski Butternut
9.0/10 (134 reviews)
Hit the slopes in Great Barrington with a visit to Ski Butternut. While you're in the area, stroll along the lakeside.
National Shrine of the Divine Mercy
9.0/10 (83 reviews)
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
Lee Premium Outlets
8.2/10 (265 reviews)
You can find the perfect gifts to bring home at Lee Premium Outlets during your trip to Lee. Amble around the area's gardens or attend a sporting event.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.