The Berkshires Vacations

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Photo by Photo courtesy of Berkshire Visitors Bureau

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Find the Best The Berkshires Vacation Packages

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 NT$3,238 per night from Nov 20 to Nov 21
NT$3,238
NT$3,959 total
Nov 20 - Nov 21
includes taxes & fees
8.6/10 Excellent! (2,135 reviews)
My room was amazing nice view of the mountains the staff were very friendly they have a beautiful indoor pool amazing hot tub and cute movie theater along with a game room and other activities

Reviewed on 2025/11/17

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
9/10 Wonderful! (758 reviews)
The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway

Reviewed on 2025/11/14

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Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
The price is NT$2,747 per night from Nov 21 to Nov 22
NT$2,747
NT$3,068 total
Nov 21 - Nov 22
includes taxes & fees
7.8/10 Good! (959 reviews)
Everything was amazing my bf did get a beer at the bar that was expired but everything else was amazing

Reviewed on 2025/11/16

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,090 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

Hardly anyone here! Great way to spend a week day, skiing and tubing!

Bousquet Ski Area

4/5(9 reviews)

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this quaint area.

Bousquet Ski Area
Rockwell called his Stockbridge studio, his “best studio yet.” The building was originally located in the backyard of his home on South Street in Stockbridge, Mass. In 1976, toward the end of his life, Rockwell left the studio and its contents to Norman Rockwell Museum. The building was cut in two and moved to the Museum’s grounds in 1986. #Details

Norman Rockwell Museum

4.5/5(193 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

Ski Butternut

4.5/5(37 reviews)

Hit the slopes in Great Barrington with a visit to Ski Butternut. While you're in the area, stroll along the lakeside.

Ski Butternut

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.