The Berkshires Vacations

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Photo by Photo courtesy of Berkshire Visitors Bureau

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Find the Best The Berkshires Vacation Packages

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 NT$2,570 per night from Aug 25 to Aug 26
NT$2,570
NT$3,195 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (1,904 reviews)
"Everything was lovely."

Reviewed on 2025/7/27

Vacation Village in the Berkshires
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 NT$5,008 per night from Aug 7 to Aug 8
NT$5,008
NT$5,594 total
Aug 7 - Aug 8
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
Nice Hotel
"All good"

Reviewed on 2025/7/27

Hotel Downstreet, Ascend Hotel Collection
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is NT$7,393 per night from Aug 11 to Aug 12
NT$7,393
NT$8,258 total
Aug 11 - Aug 12
includes taxes & fees
9.6/10 Exceptional! (474 reviews)
"We did not care for the barn door to the bathroom. Wouldn't stay closed and large gap meant a loud radio or TV required... Otherwise, our stay was great and we would definitely recommend it."

Reviewed on 2025/7/22

The Williams Inn
See all 1,113 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.

Discover the most popular places to visit in The Berkshires

Rockwell called his Stockbridge studio, his “best studio yet.” The building was originally located in the backyard of his home on South Street in Stockbridge, Mass. In 1976, toward the end of his life, Rockwell left the studio and its contents to Norman Rockwell Museum. The building was cut in two and moved to the Museum’s grounds in 1986. #Details

Norman Rockwell Museum

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum
Hardly anyone here! Great way to spend a week day, skiing and tubing!

Bousquet Ski Area

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this quaint area.

Bousquet Ski Area

National Shrine of the Divine Mercy

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.

National Shrine of the Divine Mercy

Frequently asked questions

How much does a The Berkshires vacation 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 favorite 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 vacation 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 vacationing 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 travelers.
How far in advance should I book my The Berkshires vacation?
Travelers 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 organizing 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 vacation rentals such as beachside villas and serviced residences. You've got loads of choices!
Can I choose my airline with a The Berkshires Expedia vacation 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 vacation package?
Don't stress if you're rethinking your The Berkshires vacation 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.