The Berkshires Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Photo courtesy of Berkshire Visitors Bureau

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best The Berkshires Vacation Packages

Things to do near The Berkshires

Shopping

The Berkshires offers great shopping experiences. Visit the Lee Premium Outlets, just 16.1km away, for a variety of brands. The Berkshire Mountain Country Store, located 17.7km from the area, provides unique gifts, while The Bookstore, 24.1km away, is perfect for finding literary treasures.

Recreation

Experience the artistry at Jacob's Pillow, where you can immerse yourself in dance performances surrounded by beautiful landscapes. For tranquility, visit Goose Pond Reservation, perfect for relaxation and nature walks. Enjoy a night out at the Mahaiwe Performing Arts Center, offering captivating shows in a charming setting.

Adventure

Ski Butternut, located 14.5km from The Berkshires, offers thrilling skiing experiences for all skill levels amidst stunning mountain views. For a scenic adventure, hike the Housatonic River Walk, 17.7km away, where you’ll enjoy picturesque landscapes and refreshing outdoor vibes. Otis Ridge, only 4.8km away, is another fantastic ski destination.

Nightlife

The Berkshires offer a vibrant nightlife with a mix of cultural experiences. Visit the Mahaiwe Performing Arts Center for live performances and enjoy cocktails at The Red Lion Inn's bar. For a cozy atmosphere, check out the Whiskey Room at the Barrington Stage Company for local brews and entertainment.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near The Berkshires

The Berkshires in Massachusetts offers a perfect blend of outdoor adventures and scenic beauty, making it an ideal destination for nature lovers and culture enthusiasts alike. Explore historic houses, serene lakes, and beautiful nature reserves while enjoying activities in the Berkshire Mountains. Don't miss visiting the Berkshire Museum for a cultural experience that complements the region's stunning landscapes.

  • Norman Rockwell Museum: Located 20.9km from The Berkshires, this museum celebrates the life and works of iconic American illustrator Norman Rockwell. Experience the rich culture through his famous paintings that capture everyday American life.
  • Lee Library: Situated 17.7km away, the Lee Library offers a cozy atmosphere for families and culture enthusiasts alike. Enjoy the extensive collection of books and participate in community events that foster learning and connection.
  • National Shrine of the Divine Mercy: Just 19.3km from The Berkshires, this serene shrine is a place of reflection and spirituality. Immerse yourself in the peaceful environment and appreciate the beautiful architecture and gardens dedicated to divine mercy.

Best time to go to The Berkshires

The best time to visit The Berkshires can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around The Berkshires falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around The Berkshires falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1000000000000005°C)Light RainMostly CloudySlightly LowAverage
February24.6°F (-4.1000000000000005°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.800000000000001°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnySlightly HighAverage
July70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
August68.4°F (20.200000000000003°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyAverageAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly High
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowSlightly Low
December29.5°F (-1.4°C)Light RainMostly CloudySlightly LowAverage

Tips to save on your trip to The Berkshires

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to The Berkshires during the low season (March to April and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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 ￥16,093 per night from Feb 2 to Feb 3
￥16,093
￥19,674 total
Feb 2 - Feb 3
includes taxes & fees
8.6/10 Excellent! (2,219 reviews)
Everything was great, the staff, the room, and the amenities. We will be coming back.

Reviewed on Jan 25, 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 ￥15,275 per night from Feb 2 to Feb 3
￥15,275
￥20,521 total
Feb 2 - Feb 3
includes taxes & fees
9/10 Wonderful! (821 reviews)
Friendly informed staff, super clean room, the hot chocolate machine !!!!!

Reviewed on Jan 27, 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 ￥28,812 per night from Mar 1 to Mar 2
￥28,812
￥32,184 total
Mar 1 - Mar 2
includes taxes & fees
9.6/10 Exceptional! (571 reviews)
I had a pretty exceptional stay they accommodated my requests without issue the room was clean aside from the hair in the shower, the heating system was quite loud and that woke me up multiple times throughout the night but having a charger on site for the Tesla was a big selling point for me especially ...

Reviewed on Jan 26, 2026

The Williams Inn
See all 1,080 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

4.5/5(98 reviews)

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
A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip

Tanglewood Music Center

5/5(150 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.

Tanglewood Music Center
Fall buildings

Williams College

4.5/5(176 reviews)

Take a campus tour or just explore the area of Williams College, during your travels in 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 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.

Explore a world of travel with Expedia

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