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 ₹13,338 per night from 14 Jul to 15 Jul
₹13,338
₹15,945 total
14 Jul - 15 Jul
includes taxes & fees
8.8/10 Excellent! (2,430 reviews)
"Very nice room and facility"

Reviewed on 9 Jul 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is ₹14,413 per night from 13 Jul to 14 Jul
₹14,413
₹16,099 total
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (1,013 reviews)
"Front desk staff was very accommodating. She was kind to let us check in as soon as rooms were cleaned. We traveled from California and were very sleepy and that made our stay more enjoyable."

Reviewed on 10 Jul 2026

The Yankee Inn
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 ₹12,738 per night from 10 Aug to 11 Aug
₹12,738
₹16,358 total
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (1,029 reviews)
"Very spacious. Kitchen is a plus"

Reviewed on 11 Jul 2026

Berkshire Mountain Lodge
See all 1,092 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.
See properties

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.