Berkshire County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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
FlightsFlightsHotelsHotels

Great Barrington

Great Barrington

Top Berkshire County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

3 out of 5
per person
Sep 1 - Sep 12
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
It was easy to get to Saratoga Performing Arts Center and good place to grab food or do some shopping.

Reviewed on Jul. 29, 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
Sep 1 - Sep 12
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Albany (ALB)
8.4/10 Very Good! (664 reviews)
enjoyed the sunday farmers market which was within walking distance. recommend Ambition Coffee for breakfast.

Reviewed on Jul. 27, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
per person
Sep 1 - Sep 12
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Albany (ALB)
9/10 Wonderful! (41 reviews)
beautiful location restaurant was excellent

Reviewed on Jul. 31, 2025

Microtel Inn & Suites by Wyndham Amsterdam

Microtel Inn & Suites by Wyndham Amsterdam

2.5 out of 5
per person
Sep 1 - Sep 12
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Albany (ALB)
9.4/10 Exceptional! (654 reviews)
This property is our new secret hack to attending events at SPAC. Online check in made the process quick and easy, the property is clean, safe, and incredibly convenient. Staff was friendly and on the ball. We couldn't be happier with our choice and will definitely be back when we need a place to stay in the Capitol / Saratoga area.

Reviewed on Jul. 31, 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Sep 1 - Sep 12
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Albany (ALB)
7.8/10 Good! (1,174 reviews)
You can stay there and leave your car when you fly

Reviewed on Aug. 2, 2025

Berkshire County Hotel Deals

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Sep 1 to Sep 2
CA $198
CA $221 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Staff was fine- they were fine but didn’t really go the extra mile."

Reviewed on Jul. 30, 2025

Hotel Downstreet, Ascend Hotel Collection
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Aug 17 to Aug 18
CA $117
CA $146 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,913 reviews)
Kids loved it
"Great place. Kids loved it. Friendly staff and guests."

Reviewed on Jul. 30, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Aug 24 to Aug 25
CA $131
CA $177 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (535 reviews)
"It was a great central spot for our plans in the Berkshires. The place is quiet and the staff is friendly. The rooms are very large with a stocked kitchen, dishwasher, dining table, etc. The pull out sofa has a thinner mattress so don't expect a lot of comfort, but the king bed was good. A/C could ..."

Reviewed on Jul. 31, 2025

Berkshire Mountain Lodge
See all 1,112 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Berkshire County vacation package cost?
Less than you might think — from as low as CA $1,438, 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.