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 delightful blend of outdoor activities and scenic beauty, making it perfect for adventure seekers and those looking to relax. Popular activities include skiing at various resorts, vineyard trips, and family-friendly adventures. Visitors can enjoy leisurely strolls through picturesque landscapes and explore numerous hiking trails, ensuring an unforgettable experience in this charming region of Massachusetts.

Shopping

The Berkshires offers a delightful shopping experience. At Lee Premium Outlets, just 16.1km away, you can find a variety of brands. The Berkshire Mountain Country Store, located 17.7km from The Berkshires, features unique gifts, while The Bookstore, 24.1km away, is perfect for literary finds.

Recreation

At Jacob's Pillow, immerse yourself in the world of dance amidst a vibrant cultural atmosphere. Goose Pond Reservation offers serene trails and tranquil waters, perfect for relaxation and rejuvenation. Meanwhile, the Mahaiwe Performing Arts Center provides an enchanting venue for family-friendly performances and romantic evenings.

Adventure

At Ski Butternut, located 14.5km from The Berkshires, enjoy thrilling slopes and vibrant ski culture. Otis Ridge, a mere 4.8km away, offers excellent skiing experiences. For a scenic adventure, hike the Housatonic River Walk, situated 17.7km from The Berkshires, surrounded by breathtaking landscapes.

Nightlife

The nightlife in The Berkshires offers a charming mix of sophistication and local flair. Enjoy live music at the historic Mahaiwe Performing Arts Center or unwind with cocktails at The Red Lion Inn. For a lively atmosphere, visit the dance floor at Club Helsinki, where vibrant performances abound.

*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, a picturesque region in Massachusetts, is ideal for outdoor enthusiasts and adventure seekers. Visitors can explore historic houses, serene lakes, and nature reserves that offer a blend of culture and adventure. Notable attractions include the Berkshire Museum and the scenic Berkshire Hills, providing ample opportunities for relaxation and exploration amidst stunning landscapes.

  • McLennan Reservation: Located 6.4km from The Berkshires, this serene preserve offers breathtaking scenery and a tranquil environment for nature lovers. Enjoy picturesque trails that wind through lush landscapes, making it ideal for leisurely walks and birdwatching.
  • Chesterwood: Situated 20.9km away, Chesterwood is the historic home and studio of sculptor Daniel Chester French. This site immerses visitors in rich cultural heritage, with beautifully maintained gardens and exhibitions showcasing French's iconic works, including the Lincoln Memorial.
  • National Shrine of the Divine Mercy: Just 19.3km from The Berkshires, this serene shrine serves as a place of reflection and spiritual solace. Visitors can admire stunning architecture, peaceful grounds, and participate in various religious activities, making it a culturally enriching experience.

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.

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 S$162 per night from 8 Feb to 9 Feb
S$162
8 Feb - 9 Feb
includes taxes & fees
8.6/10 Excellent! (2,221 reviews)
Everything was great, the staff, the room, and the amenities. We will be coming back.

Reviewed on 25 Jan, 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 S$169 per night from 8 Feb to 9 Feb
S$169
8 Feb - 9 Feb
includes taxes & fees
9/10 Wonderful! (828 reviews)
Only stayed for 1 night but was very impressed with this property. The room was very clean and spacious. Bed was comfortable as well. Had my two kids with me so the pool and hot tub was an amazing amenity. Left early in the morning to ski so the stay was short, but would’ve loved to stay longer and ...

Reviewed on 5 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 S$305 per night from 2 Mar to 3 Mar
S$305
2 Mar - 3 Mar
includes taxes & fees
9.6/10 Exceptional! (572 reviews)
Clean

Reviewed on 31 Jan, 2026

The Williams Inn
See all 1,088 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.