The Berkshires Trip

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Photo by Photo courtesy of Berkshire Visitors Bureau

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Things to do near The Berkshires

Shopping

Experience shopping in The Berkshires at Lee Premium Outlets, a vibrant shopping mall with a mix of entertainment and family-friendly vibes, located 16.1km away. Also visit the Berkshire Mountain Country Store and The Bookstore, both offering unique gifts and souvenirs, situated 11 and 24.1km away respectively.

Recreation

Lake Mansfield Park, located 17.7km from The Berkshires, offers a serene environment for relaxation and rejuvenation amidst nature. Jacob's Pillow, 11.3km away, combines culture and entertainment, perfect for a romantic evening. The Mahaiwe Performing Arts Center, also 17.7km distant, showcases captivating performances in a family-friendly atmosphere.

Adventure

Experience the thrill of skiing at Otis Ridge, located 4.8km from The Berkshires, where you can enjoy a lively atmosphere. For cross-country skiing, visit Maple Corner Farm, 16.1km away, or explore the scenic Housatonic River Walk, an 17.7km hike perfect for outdoor adventurers.

Nightlife

The Berkshires offer a vibrant nightlife with venues like the Mahaiwe Performing Arts Center for live performances and the Barrington Stage Company for captivating theatre. For a more relaxed evening, visit local bars like the Red Lion Inn, where you can enjoy a cosy atmosphere and good company.

*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 is an idyllic destination for outdoor enthusiasts, offering a blend of stunning scenery, adventure, and cultural experiences. Visitors can explore historic houses, tranquil lakes, and nature reserves, making it perfect for those seeking both relaxation and adventure. Notable attractions include the Berkshire Museum and the picturesque Berkshire Hills, ensuring a memorable trip for all types of travellers.

  • National Shrine of the Divine Mercy: Located 19.3km from The Berkshires, this serene shrine offers a peaceful atmosphere for reflection and spirituality. It features stunning architecture and beautiful grounds, making it an ideal spot for contemplation and connection to faith.
  • McLennan Reservation: Situated 6.4km away, this picturesque preserve boasts scenic trails and diverse wildlife. Visitors can enjoy leisurely walks surrounded by nature, with opportunities for birdwatching and photography amid the tranquil landscapes.
  • Tolland State Forest: Just 9.7km from The Berkshires, this expansive forest invites adventurers to explore its hiking trails and natural beauty. Ideal for outdoor activities, it offers a perfect setting for picnics, hiking, and immersing oneself in the great outdoors.

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 ₹10,137 per night from 29 Mar to 30 Mar
₹10,137
₹12,320 total
29 Mar - 30 Mar
includes taxes & fees
8.8/10 Excellent! (2,266 reviews)
Great! Go annually. Highly recommend

Reviewed on 25 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 ₹10,367 per night from 2 Mar to 3 Mar
₹10,367
₹13,612 total
2 Mar - 3 Mar
includes taxes & fees
9/10 Wonderful! (864 reviews)
Overcharged and lied to said security deposit was released back but never was

Reviewed on 26 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 ₹17,031 per night from 4 Mar to 5 Mar
₹17,031
₹19,023 total
4 Mar - 5 Mar
includes taxes & fees
9.6/10 Exceptional! (582 reviews)
nice aesthetics

Reviewed on 24 Feb 2026

The Williams Inn
See all 1,100 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

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
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
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.