The Berkshires Vacation Packages

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Photo by Photo courtesy of Berkshire Visitors Bureau

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Your The Berkshires Vacation

Leave the travel planning to us with a The Berkshires vacation package. With everything organized 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 organize your own customized The Berkshires vacation today.

Top The Berkshires Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

Manchester Village Historic District
CA $1,099
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
7.4/10 Good! (667 reviews)
Good

Reviewed on Oct 13, 2026

Brook Bound Inn

Brook Bound Inn

CA $1,283
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.4/10 Exceptional! (19 reviews)
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!

Reviewed on Aug 30, 2026

Wilburton Inn

Wilburton Inn

CA $1,334
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (136 reviews)
The White House Inn

The White House Inn

CA $1,242
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (361 reviews)
It was a beautiful property with friendly staff. The room was very pretty but the mattress was very soft and the pillows were tiny. We loved the fireplace as well but when you lay down you can't see the fire and it was uncomfortable to sit at the end of the bed. A cozy area should be in front of the fire place. However I would still stay there again.

Reviewed on Oct 13, 2026

The Manchester View

The Manchester View

CA $1,107
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.4/10 Exceptional! (909 reviews)
Great views !

Reviewed on Oct 13, 2026

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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
CA $115
CA $144 total
Nov 2 - Nov 3
includes taxes & fees
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
CA $122
CA $168 total
Nov 10 - Nov 11
includes taxes & fees
9/10 Wonderful! (1,204 reviews)
"We really enjoyed our stay at Berkshire Mountain Lodge. For what we paid - we absolutely feel like we got a great bang for our buck. The hotel is clean and well-maintained, and our suite was massive. It included a kitchen with all the bells and whistles (stove/stovetop, microwave, refrigerator, dishwasher), ..."

Reviewed on Oct 13, 2026

Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
CA $136
CA $152 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"They use some sort of potpourri spray and it was overwhelming. the rooms were dated and the bathrooms were very old."

Reviewed on Oct 13, 2026

The Yankee Inn
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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)
Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this family-friendly area.
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A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)
You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.
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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)
Take a campus tour or just explore the area of Williams College, during your travels in Williamstown. In the area, take in the fascinating museums and mountain views.
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A calm river surrounded by autumn foliage.
Photo by Adnan Kakazai

Norman Rockwell Museum

9.4/10 (347 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
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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)
You can spend time browsing the exhibits at Massachusetts Museum of Contemporary Art in North Adams. Take in the fascinating museums while you're in the area.
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Ski Butternut

9.0/10 (134 reviews)
Hit the slopes in Great Barrington with a visit to Ski Butternut. While you're in the area, stroll along the lakeside.
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National Shrine of the Divine Mercy

9.0/10 (83 reviews)
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.
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Lee Premium Outlets

8.2/10 (265 reviews)
You can find the perfect gifts to bring home at Lee Premium Outlets during your trip 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 vacation package cost?
We make it simple to travel somewhere new, with The Berkshires packages starting from as little as CA $1,099. 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.

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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.