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

276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
€92
31 Aug - 1 Sept
includes taxes & fees
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
€151
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (1,017 reviews)
"I thought the flowers were wood not carpet. We thought we would stay in the main building like last time. Funny smell when we first got there but I opened windows and it was better."

Reviewed on 22 Aug 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
€110
31 Aug - 1 Sept
includes taxes & fees
Berkshire Mountain Lodge
See all 1,086 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.

Stay near popular The Berkshires attractions

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)
Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.
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A hillside with autumn-colored trees and five wind turbines against a blue sky with clouds.

Jiminy Peak Mountain Resort

8.8/10 (311 reviews)
Southern New England's largest ski resort transforms into a summer playground with thrilling attractions. Glide down 45 winter trails or ride the Mountain Coaster through Berkshire Mountain scenery.
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A building with 'MASS MoCA' written on it, surrounded by greenery and hills.
Photo by Caminante

Massachusetts Museum of Contemporary Art

9.4/10 (246 reviews)
This converted factory houses one of America's largest contemporary art museums. Wander through MASS MoCA's vast industrial galleries to experience thought-provoking works that transcend artistic boundaries.
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A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

Williams College

9.4/10 (534 reviews)
Williams College offers a prestigious liberal arts education amid the scenic Berkshire Mountains. Visitors can explore the renowned Williams College Museum of Art and attend public lectures in this intellectual haven.
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A calm river surrounded by autumn foliage.
Photo by Adnan Kakazai

Norman Rockwell Museum

9.4/10 (347 reviews)
This gallery houses the world's largest collection of Norman Rockwell's iconic American illustrations. Explore his relocated studio on the scenic Berkshire estate for insight into his creative process.
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A tall, conical tower with a spherical top, surrounded by a grassy field and a stone staircase leading up to it.
Photo by Caitlin Reese

Mount Greylock

9.4/10 (180 reviews)
Massachusetts' highest peak rewards hikers with panoramic views stretching 90 miles on clear days. Explore the Appalachian Trail segment or stay overnight at the historic Bascom Lodge for a summit sunrise experience.
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National Shrine of the Divine Mercy

9.0/10 (83 reviews)
This serene sanctuary in the Berkshire Mountains is a centre for Divine Mercy devotion inspired by Saint Faustina. Visitors can join the daily 3:00 PM Chaplet or walk contemplative trails.
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Lee Premium Outlets

8.2/10 (265 reviews)
You can do some window-shopping at Lee Premium Outlets during your visit to Lee. Amble around the area's gardens or attend a sporting event.
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Frequently asked questions

How much does a The Berkshires holiday package cost?
We make it simple to travel somewhere new, with The Berkshires packages starting from as little as . You'll have the flexibility to bundle your favourite airlines, hotels and car rental. For the ultimate getaway, why not add a few tours and experiences to your itinerary?
How do I get a cheap travel package to The Berkshires?
Just imagine all the thrilling things you could do in The Berkshires with extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and extras into a The Berkshires holiday package. You have plenty of choice when you book with Expedia too. In fact, you can pick from more than 550 airlines and 1,000,000 properties around the world. Whether you're holidaying with the family or embarking on a solo adventure, exploring The Berkshires is better with a package.
What are the top hotels in The Berkshires?
Hampton Inn Boston - Logan Airport and Boston Park Plaza know how to make their guests feel welcome in Great Barrington. If you also plan to explore Hancock, have a look at Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel. Both are top picks with travellers.
How far in advance should I book my The Berkshires holiday?
Travellers are normally able to browse international flights on Expedia up to a year in advance of departure. Booking last minute? With a stroke of luck, it's still possible to purchase a cheaper ticket only weeks before your flight.
What does an Expedia The Berkshires travel package include?
Flights, hotels and a cool car for all your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to organising your The Berkshires trip, you're in charge!
What should I know before booking a The Berkshires travel package?
Booking all the parts of your trip together is a simple way to save. Combine car rentals, airfares and hotels into a tidy little package. But hotels aren't your only option. Expedia has all kinds of properties, including holiday rentals such as beachside villas and serviced residences. You've got loads of choices!
Can I choose my airline with a The Berkshires Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You're the boss! We have access to more than 550 airline partners across the globe, so you have options galore when putting together your The Berkshires escape.
If I'm not able to travel, can I cancel my The Berkshires holiday package?
Don't stress if you're rethinking your The Berkshires holiday package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We totally understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.

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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.