The Berkshires Holidays

Photo by Photo courtesy of Berkshire Visitors Bureau

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Things to do near The Berkshires

The Berkshires offers a captivating blend of outdoor adventures and cultural experiences. Visitors can enjoy skiing at local resorts or explore scenic hiking trails. Vineyard trips and leisurely strolls through picturesque landscapes are also popular. Additionally, the region is home to various cultural destinations, making it perfect for day trips that celebrate the area's rich heritage and natural beauty.

Shopping

For delightful shopping in The Berkshires, visit the Lee Premium Outlets, located 16.1km away, offering a vibrant atmosphere. The Berkshire Mountain Country Store, 17.7km distant, provides unique gifts, while The Bookstore, 24.1km away, is perfect for literary souvenirs.

Recreation

Experience the vibrant atmosphere at Jacob's Pillow, where captivating dance performances immerse you in culture and romance. For a serene escape, Goose Pond Reservation offers tranquil nature walks and relaxation amidst beautiful scenery. Enjoy family-friendly entertainment at the Mahaiwe Performing Arts Center, showcasing diverse performances in a charming setting.

Adventure

Ski Butternut, located 14.5km from The Berkshires, offers exhilarating slopes for skiing enthusiasts amidst a vibrant sports atmosphere. For a scenic adventure, the Housatonic River Walk, 17.7km away, features picturesque trails perfect for hiking and enjoying the great outdoors. Otis Ridge, merely 4.8km distant, provides another fantastic skiing experience.

Nightlife

The Berkshires offer a charming nightlife with venues like the Iron Horse Music Hall in Northampton for live music, and Barrington Stage Company in Pittsfield for theatre. Enjoy cosy pubs and fine dining in Great Barrington, where the atmosphere is vibrant yet relaxed, perfect for unwinding after a day's adventures.

*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 offers an enchanting blend of outdoor adventure and scenic beauty, ideal for those seeking a culturally rich experience. Visitors can explore historic houses, serene lakes, and nature reserves, perfect for immersing oneself in the region's charm. Notable attractions include the picturesque Berkshire Hills and the engaging Berkshire Museum, ensuring a memorable trip for every traveller.

  • National Shrine of the Divine Mercy: Situated 19.3km from The Berkshires, this serene shrine offers a peaceful atmosphere for reflection and prayer, showcasing stunning architecture and beautiful grounds that inspire a sense of spirituality and community.
  • McLennan Reservation: A mere 6.4km away, this picturesque reserve features captivating trails and diverse habitats, perfect for hiking and immersing oneself in the tranquillity of nature, with scenic views that change with the seasons.
  • Naumkeag Museum: Located 19.3km from The Berkshires, this historic house museum is renowned for its exquisite gardens and rich history, providing insight into the Gilded Age and showcasing stunning art and architecture.

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

  • 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.

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 €108 per night from 23 Feb to 24 Feb
€108
23 Feb - 24 Feb
includes taxes & fees
8.8/10 Excellent! (2,257 reviews)
The staff was wonderful and the pool was great.

Reviewed on 21 Feb 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 €127 per night from 23 Feb to 24 Feb
€127
23 Feb - 24 Feb
includes taxes & fees
9/10 Wonderful! (853 reviews)
The staff were friendly and welcoming and the rooms were spacious and clean. Pool and hot tub were fun after a long day of skiing. It was an overall great experience. The hot cocoa and coffee was a nice touch and would recommend this hotel to any skiers or snowboarders trying out the nearby ...

Reviewed on 21 Feb 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 €178 per night from 23 Feb to 24 Feb
€178
23 Feb - 24 Feb
includes taxes & fees
9.6/10 Exceptional! (577 reviews)
Elegant and oupdated decor throughout, spotlessly clean Welocation,

Reviewed on 21 Feb 2026

The Williams Inn
See all 1,089 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

National Shrine of the Divine Mercy

3/5(1 review)

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

Naumkeag Museum

You can spend time studying the exhibits at Naumkeag Museum in Stockbridge. While you're in the area, stroll along the lakeside.

Naumkeag Museum

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.