
Berkshire County Vacations & Trips from $928
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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
The Latest Berkshire County Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Lodges At Cresthaven
Price was $1,214, price is now $928 per person
$928
per person
Jun 4 - Jun 7
found 7 hours ago
Roundtrip flight included
Chicago (MDW) to Albany (ALB)
9.4/10 Exceptional! (576 reviews)
The resort was beautiful! Unfortunately the pool wasn't open yet but we understood as it was early in the season and still a bit chilly. We loved the lake view!
Reviewed on Apr 12, 2026


DoubleTree by Hilton Schenectady Downtown
Downtown
Price was $1,639, price is now $1,266 per person
$1,266
per person
Jun 20 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
8.4/10 Very Good! (760 reviews)
Bar had a good selection and friendly staff
Reviewed on May 2, 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

Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from May 24 to May 25
$126 total
May 24 - May 25
Total with taxes and fees
9/10 Wonderful! (922 reviews)
Kitchen fully equipped for basic cooking. Outdoor hot tub is nice amd hot and well maintained.
Reviewed on May 2, 2026

Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $96 total per night from May 5 to May 6
$96 total
May 5 - May 6
Total with taxes and fees
9/10 Wonderful! (928 reviews)
I frequent the Berkshires so I was very happy to discover this wonderful place on my last visit. Now, I can’t imagine staying anywhere else. The location is convenient, the rooms clean and lovely, and the staff is wonderful.
Reviewed on May 3, 2026

Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from May 4 to May 5
$123 total
May 4 - May 5
Total with taxes and fees
8.8/10 Excellent! (2,347 reviews)
Muito bom para aproveitar em família ou a 2
Reviewed on May 3, 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.
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