Berkshire County Holidays

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Your Berkshire County Holiday

With a Berkshire County holiday 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 holiday into reality.

Top destinations in Berkshire County

FlightsFlightsHotelsHotels

Great Barrington

Great Barrington

Berkshire County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Top Sights
Mount Greylock, Bash Bish Falls State Park and Natural Bridge State Park

Our pick of the best Berkshire County Hotel Deals

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 AU$269 per night from 30 June to 1 July
AU$269
30 June - 1 July
includes taxes & fees
8.8/10 Excellent! (1,015 reviews)
"This is a wonderful modern hotel in a very center of North Adams. A view from 7th floor is picturesque. It is very clean. The room is spacious; the beds are comfortable. The pool looks good, although we didn't try that. There are a coupe of nice art exhibitions on the first floor. The coffee is good, ..."

Reviewed on 15 June 2026

Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AU$224 per night from 21 June to 22 June
AU$224
21 June - 22 June
includes taxes & fees
9/10 Wonderful! (980 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."

Reviewed on 15 June 2026

Berkshire Mountain Lodge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is AU$192 per night from 23 June to 24 June
AU$192
23 June - 24 June
includes taxes & fees
8.8/10 Excellent! (2,396 reviews)
"I enjoy staying here . The front desk staff was very friendly . I like the hours of outdoor and indoor pool . My only complaints is the rooms are very very outdated and had to go to front desk every day because keys didnt work ."

Reviewed on 15 June 2026

Vacation Village in the Berkshires
See all 1,080 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 holiday package cost?
Less than you might think — from as low as , 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 holiday 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 cosy 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 holiday?
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 holiday 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 holiday 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 holiday 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 in Autumn, Lenox, Massachusetts

Tanglewood Music Center

9.6/5 (457 reviews)
You can make plans for a show at Tanglewood Music Center during your stay in Lenox. While you're in the area, stroll along the lakeside.
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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.