The Berkshires Holidays

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Photo by Photo courtesy of Berkshire Visitors Bureau

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The Berkshires Holiday

Our pick of the best The Berkshires Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
NZ$199
15 Sept - 16 Sept
includes taxes & fees
8.8/10 Excellent! (2,605 reviews)
"Everything was clean, the unit was well stocked, and the front desk staff member was excellent."

Reviewed on 5 Sept 2026

Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA
Fully refundable
NZ$272
27 Sept - 28 Sept
includes taxes & fees
Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
NZ$189
1 Oct - 2 Oct
includes taxes & fees
9/10 Wonderful! (1,124 reviews)
"it was centrally located and easy to get to and from."

Reviewed on 4 Sept 2026

Berkshire Mountain Lodge
See all 1,096 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.

Stay near popular The Berkshires attractions

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

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.
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A hillside with autumn-colored trees and five wind turbines against a blue sky with clouds.

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.
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A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

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.
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A building with 'MASS MoCA' written on it, surrounded by greenery and hills.
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.
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A tall, conical tower with a spherical top, surrounded by a grassy field and a stone staircase leading up to it.
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.
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A calm river surrounded by autumn foliage.
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.
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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.
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Lee Premium Outlets

8.2/10 (265 reviews)
You can do some window-shopping at Lee Premium Outlets during your visit to Lee. Amble around the area's gardens or attend a sporting event.
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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.