The Berkshires Vacations

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Photo by Photo courtesy of Berkshire Visitors Bureau

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Find the Best The Berkshires Vacation Packages

Things to do near The Berkshires

Shopping

The Berkshires offers great shopping experiences. Visit the Lee Premium Outlets, just 16.1km away, for a variety of brands. The Berkshire Mountain Country Store, located 17.7km from the area, provides unique gifts, while The Bookstore, 24.1km away, is perfect for finding literary treasures.

Recreation

Experience the artistry at Jacob's Pillow, where you can immerse yourself in dance performances surrounded by beautiful landscapes. For tranquility, visit Goose Pond Reservation, perfect for relaxation and nature walks. Enjoy a night out at the Mahaiwe Performing Arts Center, offering captivating shows in a charming setting.

Adventure

Ski Butternut, located 14.5km from The Berkshires, offers thrilling skiing experiences for all skill levels amidst stunning mountain views. For a scenic adventure, hike the Housatonic River Walk, 17.7km away, where you’ll enjoy picturesque landscapes and refreshing outdoor vibes. Otis Ridge, only 4.8km away, is another fantastic ski destination.

Nightlife

The Berkshires offer a vibrant nightlife with a mix of cultural experiences. Visit the Mahaiwe Performing Arts Center for live performances and enjoy cocktails at The Red Lion Inn's bar. For a cozy atmosphere, check out the Whiskey Room at the Barrington Stage Company for local brews and entertainment.

*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 offers a perfect blend of outdoor adventures and scenic beauty, making it an ideal destination for nature lovers and culture enthusiasts alike. Explore historic houses, serene lakes, and beautiful nature reserves while enjoying activities in the Berkshire Mountains. Don't miss visiting the Berkshire Museum for a cultural experience that complements the region's stunning landscapes.

  • Norman Rockwell Museum: Located 20.9km from The Berkshires, this museum celebrates the life and works of iconic American illustrator Norman Rockwell. Experience the rich culture through his famous paintings that capture everyday American life.
  • Lee Library: Situated 17.7km away, the Lee Library offers a cozy atmosphere for families and culture enthusiasts alike. Enjoy the extensive collection of books and participate in community events that foster learning and connection.
  • National Shrine of the Divine Mercy: Just 19.3km from The Berkshires, this serene shrine is a place of reflection and spirituality. Immerse yourself in the peaceful environment and appreciate the beautiful architecture and gardens dedicated to divine mercy.

Best time to go to The Berkshires

The best time to visit The Berkshires can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around The Berkshires falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around The Berkshires falls in January, 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.

The Berkshires Hotel Deals

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 ￥21,284 per night from Jul 27 to Jul 28
￥21,284
￥25,548 total
Jul 27 - Jul 28
includes taxes & fees
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
The price is ￥27,502 per night from Jul 27 to Jul 28
￥27,502
￥30,720 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"The staff was incredibly helpful and made our weekend very enjoyable. With that being said there were a couple of minor issues that we suspect will be addressed. There were not enough towels by the pool after being told they were there. The hotel doesn’t have its own restaurant but there is an attached ..."

Reviewed on Jul 10, 2026

Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
The price is ￥19,102 per night from Aug 12 to Aug 13
￥19,102
￥21,337 total
Aug 12 - Aug 13
includes taxes & fees
8.6/10 Excellent! (1,018 reviews)
"The beds are comfortable but the room was dirty - hairs in the tub and on the carpet, the cleaning staff isn't equipped with vacuum cleaners and it shows. I think the property could be easily improved"

Reviewed on Jul 13, 2026

Quality Inn Great Barrington
See all 1,091 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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Frequently asked questions

How much does a The Berkshires vacation 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 favorite 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 vacation 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 vacationing 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 travelers.
How far in advance should I book my The Berkshires vacation?
Travelers 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 organizing 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 vacation rentals such as beachside villas and serviced residences. You've got loads of choices!
Can I choose my airline with a The Berkshires Expedia vacation 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 vacation package?
Don't stress if you're rethinking your The Berkshires vacation 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.