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.
Super 8 by Wyndham Albany

Super 8 by Wyndham Albany

2 out of 5
per person
Oct 11 - Oct 18
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
6.8/10 (1,006 reviews)
Every time I stay here, I have a different experience. This was the third distinct room I've experienced. I think we got a free upgrade, from a queen to a king. What we got was a time capsule. The left side was reasonable. An old suite. Clean and appealing. The right side... where the old, unusable jacuzzi remains and a bathroom that, unlike all the other rooms I've stayed in there, needs serious renovations. Again, all other rooms have renovated bathrooms. Even the handle of the water in the shower came off. A different experience. This will be a great room should it ever be renovated.

Reviewed on Jul. 27, 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
Oct 11 - Oct 18
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
8.4/10 Very Good! (669 reviews)
enjoyed the sunday farmers market which was within walking distance. recommend Ambition Coffee for breakfast.

Reviewed on Jul. 27, 2025

Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
per person
Oct 11 - Oct 18
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
9/10 Wonderful! (940 reviews)
Our stay was very good. All staff were very helpful and friendly. The food was great and at breakfast the staff were very friendly and helpful. Our room was very clean, and our beds were very comfortable. We enjoyed our stay.

Reviewed on Jul. 30, 2025

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

3 out of 5
per person
Oct 11 - Oct 18
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
8.8/10 Excellent! (1,002 reviews)
The breakfast was great. The ladies kept the eggs coming out and the coffee was brewed to perfection. The staff were very knowledgeable; (they explained they couldn't take my AARP for a discount; I had to use it while I was booking our room. Also explained why they charged for our daughter, who is 16, again had to show when booking, everyone had a smile Our daughter & her cousin enjoyed the hot tub. The rooms, bathrooms were clean and well stocked with towels.

Reviewed on Aug. 5, 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Oct 11 - Oct 18
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
8/10 Very Good! (1,168 reviews)
Conveniently located, rural setting

Reviewed on Aug. 5, 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 $126 per night from Aug 27 to Aug 28
CA $126
CA $156 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (1,923 reviews)
"The unit has everything you need and is very clean. It would benefit from a step stool in the kitchen area because you can't reach the dishes without standing on a chair. Also it says you MUST use a convention pan to use the cooktop but there isn't one. Parking is difficult -- the spaces area too ..."

Reviewed on Aug. 3, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Aug 24 to Aug 25
CA $152
CA $201 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (537 reviews)
"Great location to stay between Tanglewood concerts. Will come again."

Reviewed on Aug. 2, 2025

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Aug 6 to Aug 7
CA $98
CA $109 total
Aug 6 - Aug 7
includes taxes & fees
5.2/10 (761 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on Aug. 2, 2025

FairBridge Inn Express
See all 1,107 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

Naumkeag Museum

You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.

Naumkeag Museum

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 $809. 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.