The Berkshires Holidays
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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
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
AU$144
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (2,724 reviews)
"The amenities are great! The gym, pool, hot tub, EV charging stations, quite equipped kitchen, and more make this hotel very appealing. However, the 4 PM check-in and 10 AM check-out times leave far too little time to enjoy everything the hotel has to offer. Everyone has different priorities when ..."
Reviewed on 11 Oct 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
AU$169
9 Nov - 10 Nov
includes taxes & fees
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
AU$170
1 Nov - 2 Nov
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.
Stay near popular The Berkshires attractions
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.
Tanglewood Music Center
9.6/10 (457 reviews)
Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.
Williams College
9.4/10 (534 reviews)
Williams College offers a prestigious liberal arts education amid the scenic Berkshire Mountains. Visitors can explore the renowned Williams College Museum of Art and attend public lectures in this intellectual haven.
Photo by Adnan Kakazai
Norman Rockwell Museum
9.4/10 (347 reviews)
This gallery houses the world's largest collection of Norman Rockwell's iconic American illustrations. Explore his relocated studio on the scenic Berkshire estate for insight into his creative process.
Photo by Caminante
Massachusetts Museum of Contemporary Art
9.4/10 (246 reviews)
This converted factory houses one of America's largest contemporary art museums. Wander through MASS MoCA's vast industrial galleries to experience thought-provoking works that transcend artistic boundaries.
Photo by Caitlin Reese
Mount Greylock
9.4/10 (180 reviews)
Massachusetts' highest peak rewards hikers with panoramic views stretching 90 miles on clear days. Explore the Appalachian Trail segment or stay overnight at the historic Bascom Lodge for a summit sunrise experience.
Ski Butternut
9.0/10 (134 reviews)
Ski Butternut offers 22 diverse trails across 110 acres of terrain suitable for all skill levels. Morning visits reward skiers with freshly groomed slopes and the satisfaction of first tracks.
National Shrine of the Divine Mercy
9.0/10 (83 reviews)
This serene sanctuary in the Berkshire Mountains is a centre for Divine Mercy devotion inspired by Saint Faustina. Visitors can join the daily 3:00 PM Chaplet or walk contemplative trails.
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.
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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.
