The Berkshires Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Photo courtesy of Berkshire Visitors Bureau

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your The Berkshires Holiday

Leave the travel planning to us with a The Berkshires holiday package. With everything organised before you head off, the only thing left for you to do is relax and enjoy this destination's countless delights. A trip to The Berkshires wouldn't be complete without exploring some of its most renowned cities, starting with Lenox. A couple of the top attractions here include National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown should also be on the itineraries of all The Berkshires travellers. Visitors to this city enjoy Massachusetts Museum of Contemporary Art and Mount Greylock. Expedia has flights, hotels, car rentals and more to help you organise your own customised The Berkshires holiday today.

The Berkshires Holiday

The Berkshires 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 The Berkshires Hotel Deals

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 AU$143 per night from 30 Nov to 1 Dec
AU$143
30 Nov - 1 Dec
includes taxes & fees
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 AU$163 per night from 12 Nov to 13 Nov
AU$163
12 Nov - 13 Nov
includes taxes & fees
9/10 Wonderful! (1,247 reviews)
"The coffee station is very unfriendly. You can only make a cup of coffee at a time. And when you have one family with multiple people it takes too much time to get one single cup of coffee so you have people frustrated. They were also draining the pool with no notification to the people staying ..."

Reviewed on 30 Oct 2026

Berkshire Mountain Lodge
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
The price is AU$112 per night from 1 Dec to 2 Dec
AU$112
1 Dec - 2 Dec
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"I booked this for one of my bus drivers & he told me he had a good time theree in the hotel. Clean & quiet."

Reviewed on 30 Oct 2026

Quality Inn Great Barrington
See all 1,097 properties in The Berkshires
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular The Berkshires attractions

A forested hillside with a clear path and a small building at the top.

Jiminy Peak Mountain Resort

8.8/10 (311 reviews)
Southern New England's largest ski resort transforms into a summer playground with thrilling attractions. Glide down 45 winter trails or ride the Mountain Coaster through Berkshire Mountain scenery.
See properties

Frequently asked questions

How much does a The Berkshires holiday package cost?
We make it simple to travel somewhere new, with The Berkshires packages starting from as little as . You'll have the flexibility to bundle your favourite airlines, hotels and car rental. For the ultimate getaway, why not add a few tours and experiences to your itinerary?
How do I get a cheap travel package to The Berkshires?
Just imagine all the thrilling things you could do in The Berkshires with extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and extras into a The Berkshires holiday package. You have plenty of choice when you book with Expedia too. In fact, you can pick from more than 550 airlines and 1 000 000 properties around the world. Whether you're holidaying with the family or embarking on a solo adventure, exploring The Berkshires is better with a package.
What are the top hotels in The Berkshires?
Hampton Inn Boston - Logan Airport and Boston Park Plaza know how to make their guests feel welcome in Great Barrington. If you also plan to explore Hancock, have a look at Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel. Both are top picks with travellers.
How far in advance should I book my The Berkshires holiday?
Travellers are normally able to browse international flights on Expedia up to a year in advance of departure. Booking last minute? With a stroke of luck, it's still possible to purchase a cheaper ticket only weeks before your flight.
What does an Expedia The Berkshires travel package include?
Flights, hotels and a cool car for all your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to organising your The Berkshires trip, you're in charge!
What should I know before booking a The Berkshires travel package?
Booking all the parts of your trip together is a simple way to save. Combine car rentals, airfares and hotels into a tidy little package. But hotels aren't your only option. Expedia has all kinds of properties, including holiday homes such as beachside villas and serviced residences. You've got loads of choices!
Can I choose my airline with a The Berkshires Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You're the boss! We have access to more than 550 airline partners across the globe, so you have options galore when putting together your The Berkshires escape.
If I'm not able to travel, can I cancel my The Berkshires holiday package?
Don't stress if you're rethinking your The Berkshires holiday package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We totally understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.