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.
Park Manor Hotel

Park Manor Hotel

4 out of 5
Price was CA $528, price is now CA $457 per person
CA $457
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
7.8/10 Good! (1,196 reviews)
Bed was comfy, great pillows, just missing breakfast

Reviewed on Feb 19, 2026

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was CA $615, price is now CA $503 per person
CA $503
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
Room was clean. Only issue was when taking a shower the water didn’t drain.

Reviewed on Feb 14, 2026

Marriott Albany

Marriott Albany

3.5 out of 5
Price was CA $701, price is now CA $584 per person
CA $584
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
8.2/10 Very Good! (751 reviews)
Clean room, friendly staff. Would stay again

Reviewed on Feb 20, 2026

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Price was CA $681, price is now CA $567 per person
CA $567
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
8/10 Very Good! (1,214 reviews)
Could use some updating Keurig coffee pot was finicky. Couldn’t get it to work some days. The water reservoir did not look clean little rusted areas in there. The creamer was spoiled. I had some issues with water dripping from the bottom of the little refrigerator areas inside were wet and you could tell they have been damaged by water in the past. I did have some plumbing issues with my tub took a shower. The water was up to my ankles, and the bottom of the tub just was not secured to whatever is underneath there. However, I did express that concern and maintenance took care of it. Overall served the purpose. It was quiet. It was nice to have the restaurant and bar downstairs. I do feel like it needs some updating and could be cleaner the rugs look like they need to be shampooed. They don’t look like they even get vacuumed. I thought it was removed, it’s just is an older hotel. I’m assuming. yes but before the price I expected a little bit more.

Reviewed on Feb 17, 2026

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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 $142 per night from Feb 23 to Feb 24
CA $142
CA $174 total
Feb 23 - Feb 24
includes taxes & fees
8.6/10 Excellent! (2,248 reviews)
Yes it was clean as usual.

Reviewed on Feb 21, 2026

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 $156 per night from Feb 23 to Feb 24
CA $156
CA $205 total
Feb 23 - Feb 24
includes taxes & fees
9/10 Wonderful! (847 reviews)
Yes great stay

Reviewed on Feb 18, 2026

Berkshire Mountain Lodge
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 $257 per night from Feb 25 to Feb 26
CA $257
CA $287 total
Feb 25 - Feb 26
includes taxes & fees
9.6/10 Exceptional! (576 reviews)
Beautiful inn, wonderful staff.

Reviewed on Feb 16, 2026

The Williams Inn
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Discover the most popular places to visit in The Berkshires

Autumn reflection while walking in the vicinity of Norman Rockwell Museum, Stockbridge. #LivingtheDream #Stockbridge #NewEngland #Reflection #Autumn #Walking

Norman Rockwell Museum

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
Hancock Shaker Village, Hancock Massachusetts beautiful place; description Shakers, all supported themselves by the proceeds of their farmland. The Hancock Shakers were primarily dairy farmers. The raising and sale of garden seeds was perhaps the most lucrative of their early businesses.Land acquisition and conversion continued for decades, with the area peaking at 3,000 acres

Hancock Shaker Village

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

National Shrine of the Divine Mercy

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

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.