The Berkshires Holidays

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Photo by Photo courtesy of Berkshire Visitors Bureau

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The Berkshires Holiday

Our pick of the best The Berkshires Hotel Deals

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 NZ$273 per night from 11 June to 12 June
NZ$273
11 June - 12 June
includes taxes & fees
9/10 Wonderful! (962 reviews)
"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope ..."

Reviewed on 4 June 2026

Berkshire Mountain Lodge
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 NZ$248 per night from 11 June to 12 June
NZ$248
11 June - 12 June
includes taxes & fees
8.8/10 Excellent! (2,389 reviews)
"Great place just listed again for four more nights"

Reviewed on 3 June 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is NZ$214 per night from 23 June to 24 June
NZ$214
23 June - 24 June
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Beautiful and well maintained and close to shipping and food"

Reviewed on 29 May 2026

The Yankee Inn
See all 1,100 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.

Discover the most popular places to visit in The Berkshires

Wide paths in the middle pf a forest shows the ski trails on the mountains in the summer

Jiminy Peak Mountain Resort

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.

Jiminy Peak Mountain Resort
Massachusetts Museum of Contemporary Art

Massachusetts Museum of Contemporary Art

You can spend time studying the exhibits at Massachusetts Museum of Contemporary Art in North Adams. Take in the fascinating museums while you're in the area.

Massachusetts Museum of Contemporary Art
Fall buildings

Williams College

Explore the campus of Williams College during your trip to Williamstown. In the area, take in the fascinating museums and mountain views.

Williams College

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 travellers 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 holiday 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 travelling 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.