Berkshire County Vacation Packages
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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 vacation destinations in Berkshire County
Great Barrington
Top Berkshire County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Manchester View
CA $1,152
per person
Oct 30 - Nov 1
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
9.4/10 Exceptional! (902 reviews)
Property has been renovated-it is very clean and modern. Nice simple breakfast served. Housekeeping didn’t show the 2nd day of our stay. ( we hunted them down for towels before getting ready for a wedding. They offered to come then- but it was too late in the day)
Great views and quite location.
Reviewed on Sep 25, 2026
Brook Bound Inn
CA $1,297
per person
Oct 30 - Nov 1
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
9.4/10 Exceptional! (19 reviews)
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!
Reviewed on Aug 30, 2026
The Equinox Golf Resort And Spa
Manchester Village Historic District
CA $1,352
per person
Oct 30 - Nov 1
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
7.4/10 Good! (665 reviews)
Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better.
Reviewed on Sep 23, 2026
Knotty Pine
CA $1,351
per person
Oct 30 - Nov 1
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
8.4/10 Very good! (154 reviews)
We arrived before check-in time, but the young woman at the front desk allowed us to get settled once our room was ready. Knowing that the cleaning staff had just finished our room, we walked in feeling comfortable that everything would be clean and ready for us. The room was quaint with a "cabin" feel--not fancy but we weren't put off by that. The bathroom floor was still wet in spots from just being mopped, but when I wiped up those wet places the bathmat I used came away dirty. It appeared that the same mop and dirty water had been used in all of the rooms. The curtain over a window in the bathroom was filthy, stained, and had several large holes in it. Truly disgusting. As we began to ready for bed, we realized that none of the pillows had cases on them. Not sure if that was just an oversight due to the rush to get our room ready for us, but needless to say, we were thankful we always travel with our own pillows. On the positive side, the young woman in the office was friendly and warm. And the bed was more comfortable than we anticipated based on the rest of the room.
Reviewed on Sep 25, 2026
Berkshire County Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
CA $135
CA $166 total
Sep 27 - Sep 28
includes taxes & fees
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
CA $111
CA $156 total
Oct 1 - Oct 2
includes taxes & fees
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
CA $143
CA $160 total
Oct 18 - Oct 19
includes taxes & 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.
Frequently asked questions
How much does a Berkshire County vacation package cost?
Less than you might think — from as low as CA $1,152, actually! By bundling hotels, flights and car rentals into a custom-made package, your Berkshire County escape is only clicks away.
How do I get a cheap travel package to Berkshire County?
Booking a Berkshire County vacation package with Expedia is a smart way to save. We have over 550 air carriers and 1,000,000 hotel options globally. With such a fabulous range to choose from, you'll have no trouble creating your dream adventure.
What are the top hotels in Berkshire County?
For properties in Great Barrington with cozy beds and friendly service, look up Hampton Inn Boston - Logan Airport and Boston Park Plaza. If you're visiting Hancock as well, you can look forward to a good night's sleep at Hilton Boston Logan Airport or Sheraton Boston, a Marriott Hotel.
How far in advance should I book my Berkshire County vacation?
While not all air carriers release ticket prices early, it's usually possible to compare international airfares on Expedia up to a year in advance. This is the time when you can score some fantastic deals. If you've left everything to the last minute, you might still be in luck. Low prices occasionally emerge a few weeks before departure.
What does an Expedia Berkshire County travel package include?
Choose from a combination of hotels, flights and rental cars. Once you've made your booking, you can add some activities and experiences. Want to pick your fare class? That's easily done too. The choice is yours when it comes to arranging your perfect Berkshire County getaway.
What should I know before booking a Berkshire County travel package?
Our prices are already low. However, you'll score even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Berkshire County Expedia vacation package?
Most definitely. Expedia has over 550 airline partners to choose from around the world. With so many choices, finding the ideal carrier to get you to Berkshire County will be easy.
If I'm not able to travel, can I cancel my Berkshire County vacation package?
It's difficult to predict what tomorrow might bring, so it's comforting to know that you can change or cancel your Berkshire County vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for further details.
Stay near popular Berkshire County attractions
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.
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.
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 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.
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 Caitlin Reese
Mount Greylock
9.4/10 (180 reviews)
Explore the great outdoors at Mount Greylock and enjoy the mountain views during your trip to Adams. You can seek out the ski slopes while 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
