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.
Hyatt Place Saratoga Malta

Hyatt Place Saratoga Malta

3 out of 5
Price was CA $1,847, price is now CA $1,528 per person
CA $1,528
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Albany (ALB)
9/10 Wonderful! (1,016 reviews)
The staff was very helpful an I had a quick check in. The room was clean. I like a hot breakfast and it was delicious, I really appreciate that the scrambled eggs where nor just plain but that they had chives. It was easy to find parking close to the door. What I did not like is the design of the shower door. It is not a door that closes fully and it ended up creating a lot of water outside of the shower. Other than that, our stay was great and I will go back again!

Reviewed on Jun 24, 2026

Bluebird Spa City Motor Lodge

Bluebird Spa City Motor Lodge

3 out of 5
Downtown Saratoga Springs
Price was CA $2,048, price is now CA $1,740 per person
CA $1,740
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Grande Prairie (YQU) to Albany (ALB)
9/10 Wonderful! (920 reviews)
This is a hidden gem. The location is right in the heart of town, so convenient to everything. They also have great spaces to enjoy your down time. The patio with fire pit overlooking Broadway was amazing. Top it with friendly attentive staff and your set. We will be back.

Reviewed on Jun 18, 2026

Sunshine Inn

Sunshine Inn

2 out of 5
Price was CA $1,914, price is now CA $1,633 per person
CA $1,633
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Albany (ALB)
No reviews
Motel 6 Lake George, NY – Adirondacks

Motel 6 Lake George, NY – Adirondacks

2.5 out of 5
Price was CA $1,882, price is now CA $1,627 per person
CA $1,627
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Albany (ALB)
9/10 Wonderful! (186 reviews)
This was a clean place and the staff was extremely helpful. I was unable to check in before check in time was closed and they accommodated me to allow my boyfriend to be the one to come check in instead of me.

Reviewed on Jun 14, 2026

Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was CA $2,224, price is now CA $1,950 per person
CA $1,950
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Albany (ALB)
9.2/10 Wonderful! (1,010 reviews)
Property was very clean and well cared for. Shuttle service was a great added bonus too!

Reviewed on Jun 25, 2026

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The Berkshires Hotel Deals

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is CA $218 per night from Jun 30 to Jul 1
CA $218
CA $244 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"No real breakfast"

Reviewed on Jun 21, 2026

Hotel Downstreet, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Jul 8 to Jul 9
CA $203
CA $227 total
Jul 8 - Jul 9
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"The hot tub was welcomed after a long day of hiking the Berkshires!"

Reviewed on Jun 26, 2026

The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
The price is CA $168 per night from Jul 26 to Jul 27
CA $168
CA $187 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain ..."

Reviewed on Jun 22, 2026

Quality Inn Great Barrington
See all 1,087 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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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

9.6/5 (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.
See properties

Frequently asked questions

Can I cancel my flight booking to The Berkshires due to COVID-19?
If you've yet to book your tickets, read the terms and conditions of the airline you're considering. If you've already secured your flight to The Berkshires, make use of our Customer Service Portal. It has information that will help you determine which COVID-19 policies are applicable to your reservation and provide you with the next steps.
What's the best way to find cheap flights to The Berkshires that have flexible change policies?
At Expedia, we've been channeling our inner yogi to give you the most flexible airfares in town. Simply tick the "No change fee" box directly below the "Flexible change policies" heading to find your dream flight to The Berkshires.
What are some of the general tips for travelers to The Berkshires during the COVID-19 outbreak?
The COVID-19 outbreak has brought about substantial changes to the way we travel. If you plan to visit The Berkshires, the following tips will help you navigate these new challenges and rules:
  • Find out if any travel restrictions apply to your destination and origin before locking in your flight. Also check if there are any requirements you'll have to follow on arrival, such as testing and quarantining.
  • You're required to wear a face mask at the airport, including at security checkpoints. Be prepared to adjust your mask to verify your identity when asked.
  • Do not hand your boarding pass directly to a TSA officer. Rather, you should position the pass on the scanner and then hold it up for the agent to visually inspect it.
  • One container of liquid hand sanitizer is now permitted in your carry-on baggage. It must not be larger than 12 oz (350 ml), and you'll need to remove it from your bag for X-ray scanning.
  • Put any personal items (like your phone and wallet) in your carry-on rather than a bin to minimize handling during screening.
  • Transport any food items in a clear plastic bag and also place them in a screening bin. Keeping food separate from your carry-on means it's less likely a TSA officer will need to open your bag for inspection.

Which airlines fly to The Berkshires?
Arrange your airfare with American Airlines and then start planning your The Berkshires to-do list. This popular carrier runs 607 flights each month to Bradley Intl. Airport (BDL), a main gateway.
How can I find cheap tickets to The Berkshires?
One of the best ways to nab cheap tickets to The Berkshires is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. You'll see the cheapest prices for nearby days. The lowest price for a flight to The Berkshires in the last seven days was . Booking ahead will usually help you get an even better deal.
How much is a flight to The Berkshires?
You could have nabbed a return flight to The Berkshires from anywhere between and in the last seven days. For one-way trips departing from (), the lowest price during this time was .
What are the most popular airports to fly into in The Berkshires?
The Berkshires's main entryway is Bradley Intl. Airport (BDL). Get your next thrilling journey underway by booking a ticket on one of the 2149 flights a month to this destination.
When is the cheapest time to fly to The Berkshires?
If you'd rather spend your vacation money enjoying the delights of The Berkshires rather than on getting there, leave early in the week. The cheapest day to fly is generally Tuesday, with Monday a close second. With many folks traveling over the weekend, Saturday often has the highest airfares.
How much is a plane ticket to The Berkshires?
In the last seven days, airfares varied between and . Swipe through our terrific deals to The Berkshires, make a booking and then start packing your suitcase.
Which airlines with flights to The Berkshires employ COVID-19 cleanliness policies?
In response to the COVID-19 pandemic, the majority of airlines have adopted new rules and measures to help their passengers and staff fly with confidence. Here are just a few examples:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.