
Berkshire County Vacations & Trips from $572
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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.

Hotel Vervana, Trademark Collection by Wyndham
$572
per person
Jan 14 - Jan 17
found 5 hours ago
Roundtrip flight included
Philadelphia (PHL) to Albany (ALB)
8.2/10 Very Good! (1,009 reviews)
The woman who checked us in was courteous and friendly but neglected to tell us that we needed to request that our room be given housekeeping while we were there. So the room was just as we left it when we returned in the afternoon. We were amazed as this was unheard of in our extensive travel experience.
When we went to check out there was a different woman at the desk chatting with 2 other employees. I was ignored until I asked why our room hadn't been attended to the day before, she told me I should have signed up to have it done when I checked in. I said Noone had suggested this when I checked in. She shrugged, made no apology for this and justified went on chatting with her fellow workers. Forget about customer service, these folks have never heard of it! The breakfast was poor. We would never go back, which is a shame because it's conveniently located.
Reviewed on Oct 23, 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
$117 nightly
$131 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (2,782 reviews)
"Very easy check in. Clean and safe."
Reviewed on Oct 23, 2026

Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$110 nightly
$123 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,224 reviews)
"Wonderful place to stay for short or long time. Everything is just perfect."
Reviewed on Oct 23, 2026

Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
$77 nightly
$86 total
Nov 15 - Nov 16
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Clean large room. Nice bathroom Walling distance to downtown and many restaurant options."
Reviewed on Oct 23, 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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