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.
Weathervane Motel

Weathervane Motel

CA $1,024
per person
Sep 17 - Sep 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
6.8/10 (790 reviews)
The room was clean, but very run down — soft uneven floors, very out of date decor, musty smell. Staff is courteous and helpful. Air conditioning was cold and effective. Water pressure strong, hot water plentiful. Parking was ample. The environment felt safe, as does most of Vermont, but the door lock was old and not strong, I didn’t leave any valuables in the room while I was out. And the security deadbolts did not work at all. I probably wont stay there again as there are better options similarly priced in the area. But if you have to, it’s at least clean.

Reviewed on Aug 10, 2026

The White House Inn

The White House Inn

CA $1,473
per person
Sep 24 - Sep 27
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (340 reviews)
This is a beautiful property with a clean and friendly staff. Impeccably maintained! The dinner we had in the dining room was excellent. The only complaint I have is that my room could have used another bar of soap, and that's no biggie!

Reviewed on Aug 9, 2026

Toll Road Inn

Toll Road Inn

CA $1,364
per person
Sep 17 - Sep 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (531 reviews)
Loved our stay, Clean and really nice Inn. Directly across the street from a diner also which was perfect.

Reviewed on Aug 7, 2026

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

CA $1,369
per person
Sep 24 - Sep 27
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.2/10 Very good! (983 reviews)
Property is very run down. Our room was filthy. Bedding stained, toilet seat stained and floor was extremely dirty. My kids were very much looking forward to the fishing pond advertised as an amenity. Unfortunately the dock was sinking, a rowboat was full of water and beer cans, and the pond was covered entirely in weeds. We didn’t even stay the night.

Reviewed on Aug 9, 2026

Sun Lodge, an Ascend Collection Hotel

Sun Lodge, an Ascend Collection Hotel

Bromley Mountain
CA $1,348
per person
Sep 17 - Sep 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (341 reviews)
Na

Reviewed on Aug 7, 2026

Ready to book your vacation to The Berkshires?

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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 $131
CA $162 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (2,517 reviews)
"Pensamos volver pronto"

Reviewed on Aug 10, 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
CA $198
CA $221 total
Aug 12 - Aug 13
includes taxes & fees
9.2/10 Wonderful! (1,021 reviews)
"Clean room, friendly staff, ample breakfast"

Reviewed on Aug 10, 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
CA $132
CA $178 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (1,059 reviews)
"Great, spacious accommodation near many things and perfect for Tanglewood concert. Loved the room, the coffee in the lobby, and all the amenities. Would stay again and again"

Reviewed on Aug 9, 2026

Berkshire Mountain Lodge
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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)
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 hillside with autumn-colored trees and five wind turbines against a blue sky with clouds.

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 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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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 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)
Explore the great outdoors at Mount Greylock and enjoy the mountain views during your trip to Adams. You can seek out the ski slopes while in the area.
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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 $1,024. 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.