Berkshire County Vacations & Trips from $595
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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
Williamstown
The Latest Berkshire County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sundowner on Lake George
Price was $815, price is now $652 per person
$652
per person
Nov 27 - Nov 30
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
7.4/10 Good! (242 reviews)
I have been traveling to Lake George for years as I love the beauty and activities of this area. Normally hotel stays are ok and nothing really wows me. Most need updating. I stayed at the Sundowner and was so pleased with everything! The rooms are updated and are decorated like adorable log cabins inside. The room was spotless and spacious! The staff were friendly and accommodating. We had a small issue with air conditioning and they sent someone right away to fix it. Kima at reception desk and Jay Jay in property management really impressed me with their friendly demeanor and seemed interested in making sure we had a great time. Kayaks and paddleboards were free and other hotels charge a few. Will definitely be back again!! Great job done by the Sundowner team.
Reviewed on Aug 11, 2025
Berkshire County Hotel Deals
Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Sep 7 to Sep 8
$170 total
Sep 7 - Sep 8
Total with taxes and fees
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $145 total per night from Sep 14 to Sep 15
$145 total
Sep 14 - Sep 15
Total with taxes and fees
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
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.
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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.