The Berkshires Vacation Packages

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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.
Baymont by Wyndham Latham Albany Airport

Baymont by Wyndham Latham Albany Airport

2.5 out of 5
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
6.2/10 (1,368 reviews)
Tough start. Read the reviews about moldy rooms. I get it now. Our first room had a bathroom that required complete renovation or condemnation. Mildew across the entire ceiling. We were given a new room, yay! The bathroom was an upgrade, but still had problems namely a toilet that had been sprayed down with blue cleaner but not wiped up. Room itself was great. It was my third stay there. Before it was just a dilapidated hallway. That was ok To deal with. Bathrooms are not. Still a reasonable place, with the right room, for one person who needs to hold over for 12 or less hours. Not recommended for more than a one night stay.

Reviewed on Jul. 13, 2025

Park Manor Hotel

Park Manor Hotel

4 out of 5
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.2/10 Very Good! (1,113 reviews)
We have a great time

Reviewed on Jul. 19, 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.8/10 Good! (1,174 reviews)
Can’t beat the convenience to the airport. The staff is always pleasant and helpful. Have stayed here the night before an early flight many times.

Reviewed on Jul. 14, 2025

Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Downtown Albany
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,007 reviews)
It was clean and room was spacious. Only thing missing was a pool.

Reviewed on Jul. 15, 2025

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,001 reviews)
The staff accommodated my needs when I missed my flight. It was safe and clean in the area.

Reviewed on Jul. 18, 2025

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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 CA $118 per night from Jul 20 to Jul 21
CA $118
CA $147 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (1,883 reviews)
"This is a great get away! Beautiful atmosphere and lots of variety of activities"

Reviewed on Jul. 17, 2025

Vacation Village in the Berkshires
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $325 per night from Aug 18 to Aug 19
CA $325
CA $364 total
Aug 18 - Aug 19
includes taxes & fees
9.6/10 Exceptional! (469 reviews)
"Hrwat"

Reviewed on Jul. 11, 2025

The Williams Inn
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 CA $221 per night from Aug 18 to Aug 19
CA $221
CA $246 total
Aug 18 - Aug 19
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Great place"

Reviewed on Jul. 16, 2025

Hotel Downstreet, Ascend Hotel Collection
See all 1,104 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.

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Discover the most popular places to visit in The Berkshires

Norman Rockwell Museum

Norman Rockwell Museum

4.5/5(6 reviews)

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

National Shrine of the Divine Mercy

5/5(1 review)

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

Hancock Shaker Village

4.5/5(3 reviews)

You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.

Hancock Shaker Village

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 $891. 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.