Berkshire County Vacations & Trips from $746
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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.
Albany Airport Inn
$746
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
6.6/10 (1,023 reviews)
Reserved for 3 nights due to death in family. Checked in at 9:30pm (day 1), checked out 8am (day 2). Filthy room, door locks broken, bathroom clearly not cleaned after last person. This was also a hotel for longer term residents (school bus in parking lot picking up children living there, one man in lobby begging to be allowed to stay after his 60 days had expired). Safety and cleanliness issues would have afforded this hotel 0 stars if possible.
Reviewed on Oct 20, 2026
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area
$778
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
8.6/10 Excellent! (1,232 reviews)
The hotel, staff, and breakfast were very nice, but our room could have been cleaner. The floor in the bathroom was dirty; someone's contact was still on the floor and there were stains on the bedding.
Reviewed on Oct 20, 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! (2,768 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
$115 nightly
$128 total
Nov 18 - Nov 19
Total with taxes and fees
9/10 Wonderful! (1,217 reviews)
"Everything was great , perfect."
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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