The Berkshires Holidays

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Your The Berkshires Holiday

Embark on your next adventure with a The Berkshires holiday package, and leave knowing the finer details are organised. And with the ability to tailor your getaway, it'll be one to remember! Your trip to The Berkshires wouldn't be complete without getting to some of its leading cities, starting with Lenox. Some of the most popular attractions here include National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown is another favourite with The Berkshires travellers. Visitors to this destination love Massachusetts Museum of Contemporary Art and Mount Greylock. Quit dreaming and get packing, because your The Berkshires holiday is only a few clicks away with Expedia.

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Things to do near The Berkshires

The Berkshires offers a delightful blend of outdoor adventures and scenic beauty, ideal for a memorable vacation. Visitors can enjoy skiing at local resorts, explore picturesque hiking trails, and embark on enjoyable vineyard trips. Additionally, leisurely strolls through charming towns and engaging day trips enhance the experience, making it a perfect destination for those seeking both relaxation and adventure.

Shopping

Visit Hoffman's Pottery, located 25.7km from The Berkshires, for unique handcrafted items. Lee Premium Outlets, 16.1km away, offers a variety of brand-name shops in a vibrant environment. Don't miss the Berkshire Mountain Country Store, 17.7km from The Berkshires, for charming gifts and local goods.

Recreation

Explore Lake Mansfield Park, a serene recreational area perfect for relaxation and rejuvenation amidst nature. Experience the enchanting performances at Jacob's Pillow, a cultural hub for dance, or enjoy a captivating show at the Mahaiwe Performing Arts Center, where family-friendly entertainment meets romance and culture.

Adventure

Experience the scenic Housatonic River Walk, an invigorating hiking trail located 17.7km from The Berkshires, perfect for outdoor enthusiasts. Enjoy thrilling skiing at Blandford Ski Area, 19.3km away, or at Ski Butternut, 14.5km from The Berkshires, where the sports vibes are electric.

Nightlife

The Berkshires offers a charming nightlife with venues like the vibrant Barrington Stage Company for live theatre and the intimate Club Helsinki for music. Enjoy a relaxed evening at the Tavern at the Aloha or sip cocktails at the picturesque Red Lion Inn, perfect for unwinding after a day of exploration.

*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 a fantastic destination for outdoor and adventure enthusiasts, offering stunning scenery and a rich cultural experience. Explore historic houses, serene lakes, and the local library, while also visiting the picturesque Berkshire Hills and the intriguing Berkshire Museum. These attractions provide a perfect blend of nature and culture, making your visit to The Berkshires truly memorable.

  • Norman Rockwell Museum: Nestled 20.9km from The Berkshires, this museum showcases the charming and nostalgic works of Norman Rockwell, capturing the spirit of American culture and everyday life. Visitors will enjoy a variety of exhibitions and a serene outdoor sculpture garden.
  • Ventfort Hall Mansion and Gilded Age Museum: Located 24.1km away, this historic mansion offers a glimpse into the opulent lifestyle of the Gilded Age. With its stunning architecture and richly decorated interiors, it's a perfect place for history enthusiasts.
  • National Shrine of the Divine Mercy: Situated 19.3km from The Berkshires, this serene shrine provides a tranquil space for reflection and prayer, featuring beautiful gardens and inspiring religious art.

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 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 Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)

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 £93 per night from 22 Feb to 23 Feb
£93
22 Feb - 23 Feb
includes taxes & fees
8.6/10 Excellent! (2,227 reviews)
Spacious 2 bed 2 bath!

Reviewed on 3 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 £110 per night from 17 Feb to 18 Feb
£110
17 Feb - 18 Feb
includes taxes & fees
9/10 Wonderful! (838 reviews)
Perfect location, big rooms, nice staff.

Reviewed on 10 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 £150 per night from 11 Mar to 12 Mar
£150
11 Mar - 12 Mar
includes taxes & fees
9.6/10 Exceptional! (573 reviews)
A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff.

Reviewed on 7 Feb 2026

The Williams Inn
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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
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
Autumn reflection while walking in the vicinity of Norman Rockwell Museum, Stockbridge. #LivingtheDream #Stockbridge #NewEngland #Reflection #Autumn #Walking

Norman Rockwell Museum

5/5(1 review)

You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell 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. Flight-inclusive packages are ATOL protected.