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

FlightsFlightsHotelsHotels

Great Barrington

Great Barrington

Top Berkshire County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was CA $1,202, price is now CA $1,005 per person
CA $1,005
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
My partner and I just moved back to MA so we are local to the area. We have stayed there just to have an evening of respite together and solo and send our family there during holidaze! Very friendly staff, comfortable rooms, prime location, and breezy breakfast options.

Reviewed on May 8, 2026

Residence Inn by Marriott Albany East Greenbush/Tech Valley

Residence Inn by Marriott Albany East Greenbush/Tech Valley

3 out of 5
Price was CA $2,059, price is now CA $1,611 per person
CA $1,611
per person
Jul 29 - Aug 4
found 6 hours ago
Roundtrip flight included
Kitchener (YKF) to Albany (ALB)
8.8/10 Excellent! (244 reviews)
Excellent property, good breakfast, nice size pool, excellent staff.

Reviewed on Apr 13, 2026

Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was CA $2,041, price is now CA $1,691 per person
CA $1,691
per person
Jul 29 - Aug 4
found 6 hours ago
Roundtrip flight included
Kitchener (YKF) to Albany (ALB)
8.8/10 Excellent! (1,057 reviews)
We had to switch rooms due to a leaking shower. Somehow it was leaking into the room. Additionally the shower was “handicap” accessible but also sprayed water all over the bathroom floor. However they immediately moved us upon complaint.

Reviewed on Apr 20, 2026

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was CA $1,941, price is now CA $1,643 per person
CA $1,643
per person
Jul 29 - Aug 4
found 6 hours ago
Roundtrip flight included
Kitchener (YKF) to Albany (ALB)
8.8/10 Excellent! (1,004 reviews)
Staff was great. Bathrooms could use a little upkeep.

Reviewed on May 1, 2026

Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was CA $1,966, price is now CA $1,676 per person
CA $1,676
per person
Jul 29 - Aug 4
found 6 hours ago
Roundtrip flight included
Kitchener (YKF) to Albany (ALB)
8.8/10 Excellent! (1,000 reviews)
Very close to Troy Theater, nice location , beautiful view of water & right next to a BBQ place .

Reviewed on May 12, 2026

Berkshire County Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is CA $120 per night from May 24 to May 25
CA $120
CA $165 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (931 reviews)
These are all 1 bedroom suites. There was plenty of room in kitchen cupboards for our groceries. The kitchen was well supplied with cooking utensils, dishes and glassware. The location is excellent with several grocery stores and restaurants close by. Everything was perfect except for the height ...

Reviewed on May 11, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
The price is CA $137 per night from May 26 to May 27
CA $137
CA $153 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (940 reviews)
Place was clean, staff very helpful and was a great place overall to stay. I liked that there was a bottle of water when I arrived and the soaps and lotions were great. There was a faint smell of dog pee near the desk area however and two days in a row they did not put out hot water for tea, which ...

Reviewed on May 12, 2026

Berkshires Untold
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
The price is CA $196 per night from Jun 3 to Jun 4
CA $196
CA $219 total
Jun 3 - Jun 4
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
Clean room...

Reviewed on May 12, 2026

Hotel Downstreet, an Ascend Collection Hotel
See all 1,124 properties in Berkshire County
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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Frequently asked questions

How much does a Berkshire County vacation package cost?
Less than you might think — from as low as CA $1,005, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.