The Berkshires Holidays

Photo by Photo courtesy of Berkshire Visitors Bureau

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Things to do near The Berkshires

Shopping

Visit Lee Premium Outlets, a vibrant shopping destination 16.1km from The Berkshires, offering a mix of brands and entertainment. For unique gifts, check out the Berkshire Mountain Country Store, located 17.7km away, and The Bookstore, 24.1km from The Berkshires, perfect for literary finds.

Recreation

Experience the captivating performances at Jacob's Pillow, where dance meets culture just 11.3km away. Unwind at Goose Pond Reservation, a serene recreational area 12.9km distant, perfect for relaxation. Enjoy family-friendly shows at the Mahaiwe Performing Arts Center, located 17.7km away, blending entertainment and culture.

Adventure

At Ski Butternut, 14.5km from The Berkshires, enjoy exhilarating skiing and snowboarding in a vibrant atmosphere. Otis Ridge, only 4.8km away, offers fantastic slopes for skiing enthusiasts. For a scenic hike, explore the Housatonic River Walk, located 17.7km away, where adventure meets breathtaking outdoor beauty.

Nightlife

The Berkshires boasts a vibrant nightlife with a mix of cosy pubs and live music venues. Visit the Colonial Theatre for captivating performances, or unwind at the Barrington Brewery for delightful craft beers. For a lively atmosphere, check out the Club Helsinki for live music and delicious dining options.

*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 is an ideal destination for outdoor enthusiasts, offering stunning scenery and a range of adventure activities. Explore historic houses, serene lakes, and nature reserves that cater to both cultural and adventurous travellers. Don't miss the Berkshire Museum and the picturesque Berkshire Hills while immersing yourself in the region's natural beauty and heritage.

  • Berkshire Botanical Garden: Nestled 20.9km from The Berkshires, this enchanting botanical garden offers a serene escape with its vibrant flora and tranquil landscapes. Perfect for romantic strolls or family outings, visitors can immerse themselves in nature's beauty while enjoying seasonal displays and themed gardens.
  • W.E.B. Du Bois Boyhood Homesite: Located 20.9km away, this historic site celebrates the early life of the influential African American scholar W.E.B. Du Bois. Experience the rich cultural history and learn about his contributions to civil rights and social justice in an engaging environment.
  • Chesterwood: Also situated 20.9km from The Berkshires, Chesterwood is the former summer home and studio of sculptor Daniel Chester French. Visitors can explore the beautifully preserved site and appreciate its cultural significance, along with stunning gardens and outdoor sculptures.

Best time to go to The Berkshires

The best time to visit The Berkshires is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to The Berkshires.
  • Consider traveling during the off-peak season (typically March to April and November) for more affordable package holidays to The Berkshires.
  • 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.

Top hotels in The Berkshires

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 HK$813 per night from 12 Mar to 13 Mar
HK$813
HK$994 total
12 Mar - 13 Mar
includes taxes & fees
8.8/10 Excellent! (2,296 reviews)
The pool was very nice.The glass wall gives a beautiful view

Reviewed on 11 Mar 2026

Vacation Village in the Berkshires
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 HK$924 per night from 5 Apr to 6 Apr
HK$924
HK$1,033 total
5 Apr - 6 Apr
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options.

Reviewed on 5 Mar 2026

Hotel Downstreet, an Ascend Collection Hotel
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 HK$832 per night from 2 Apr to 3 Apr
HK$832
HK$1,104 total
2 Apr - 3 Apr
includes taxes & fees
9/10 Wonderful! (871 reviews)
the room was huge - we loved it!!

Reviewed on 11 Mar 2026

Berkshire Mountain Lodge
See all 1,112 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.

Popular places to visit

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

Tanglewood Music Center

4/5(1 review)

You can make plans for a show at Tanglewood Music Center during your stay in Lenox. While you're in the area, stroll along the lakeside.

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

Jiminy Peak Mountain Resort

4/5(1 review)

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
View of MassMoca from bridge

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

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.