Berkshire County Vacations & Trips from $563
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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.
Best Western Plus Franklin Square Inn Troy/Albany
$653
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
8.8/10 Excellent! (1,005 reviews)
Everything was fine aside from the internet connection, which I needed for work. While the internet did work, it was extremely slow and made it impossible to complete my work. I spent an hour trying to upload photos to a gallery and only made it through 23 photos.. I went home and was able to upload 50 photos in literally 30 seconds.
Reviewed on Oct 15, 2026
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area
$602
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
8.6/10 Excellent! (1,232 reviews)
BREAKFAST WAS ABUNDANT. STAFF WAS FRIENDLY AND HELPFUL. ONLY ONE PROBLEM ---THE PILLOWS WERE SO HARD. THERE WERE NO SUBSTITUTES.
Reviewed on Oct 19, 2026
Hyatt Place Albany/Downtown
Downtown Albany
$628
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
9.2/10 Wonderful! (1,884 reviews)
The room was clean, the staff was helpful and friendly, and the breakfast was good. Overall, a pleasant stay!
Reviewed on Oct 19, 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
$126 nightly
$140 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (2,767 reviews)
"Amazing experience, Great for families,nearby many trails and scenic driveway! Will be back certainly"
Reviewed on Oct 19, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$114 nightly
$127 total
Nov 19 - Nov 20
Total with taxes and fees
9/10 Wonderful! (1,216 reviews)
"Large , clean suite .well equipped kitchen. Comfortable stay! Would definitely return."
Reviewed on Oct 19, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$101 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
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.