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Your The Berkshires Vacation

Leave the travel planning to us with a The Berkshires vacation package. With everything organized before you head off, the only thing left for you to do is relax and enjoy this destination's countless delights. A trip to The Berkshires wouldn't be complete without exploring some of its most renowned cities, starting with Lenox. A couple of the top attractions here include National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown should also be on the itineraries of all The Berkshires travelers. Visitors to this city enjoy Massachusetts Museum of Contemporary Art and Mount Greylock. Expedia has flights, hotels, car rentals and more to help you organize your own customized The Berkshires vacation today.

The Latest The Berkshires vacation packages

Price found within the past 48 hours. Click for updated prices.
The Equinox Golf Resort & Spa
Hotel Brookmere & Arbor Spa
27 Lincoln
Lodges At Cresthaven
La Quinta Inn & Suites by Wyndham Lake George
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Discover the most popular places to visit in The Berkshires

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
$130 nightly
The price is $145 total per night from Aug 28 to Aug 29
$145 total
Aug 28 - Aug 29
Total with taxes and fees
8.6/10 Excellent! (1,970 reviews)
"The staff at Vacation Village are simply amazing! Super nice and very helpful. Very clean, lots of amenities, and spacious rooms! Will definitely stay again!"

Reviewed on Aug 24, 2025

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
$108 nightly
The price is $120 total per night from Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (586 reviews)
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."

Reviewed on Aug 23, 2025

Berkshire Mountain Lodge
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Sep 9 to Sep 10
$104 total
Sep 9 - Sep 10
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"Great location and close enough to walk to shops and restaurants."

Reviewed on Aug 22, 2025

Quality Inn
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.

Things to do near The Berkshires

The Berkshires offers a perfect blend of outdoor adventures and scenic beauty. Visitors can enjoy skiing at various resorts, explore beautiful hiking trails, and take in stunning views on scenic drives. The area also provides ample recreation opportunities and nearby attractions, making it an ideal destination for those seeking a beach vacation or outdoor activities. Whether you're hitting the slopes or enjoying a leisurely hike, The Berkshires has something for everyone.

Shopping

The Berkshires offers a delightful shopping experience. Visit the Lee Premium Outlets, just 10 miles away, for a variety of brand-name bargains. For unique gifts, explore the Berkshire Mountain Country Store and The Bookstore, both within a short drive, showcasing local crafts and literature.

Recreation

Experience the vibrant arts at Jacob's Pillow, where you can enjoy world-class dance performances amid a culturally rich atmosphere. For relaxation, Goose Pond Reservation offers serene nature trails and tranquil waters perfect for unwinding. Don't miss the Mahaiwe Performing Arts Center for family-friendly shows in an enchanting setting.

Adventure

Ski Butternut offers an exhilarating skiing experience located 9 miles from The Berkshires, perfect for winter sports enthusiasts. For a scenic hike, explore the Housatonic River Walk, located 11 miles away, showcasing stunning views and outdoor adventure. Otis Ridge, a skiField 3 miles from The Berkshires, is ideal for skiing fun.

Nightlife

The Berkshires offer a vibrant nightlife with cozy pubs and live music venues. Enjoy craft cocktails at 20 Railroad Street or catch a show at the Mahaiwe Performing Arts Center. For a laid-back atmosphere, visit The Marketplace for local brews and delicious bites. Experience the charm of this beautiful region.

*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 adventure, scenic beauty, and cultural experiences. Visitors can explore historic houses, picturesque lakes, and local libraries while enjoying the stunning Berkshire Mountains. Don't miss the chance to visit the Berkshire Museum for a deeper insight into the region's history and art. Whether you're seeking adventure or a relaxing getaway, The Berkshires has something for everyone.

  • National Shrine of the Divine Mercy: Located 12 miles from The Berkshires, this serene shrine offers a peaceful atmosphere for reflection and prayer. Visitors can explore beautiful grounds and attend mass, immersing themselves in its rich spiritual culture.
  • Otis Reservoir: Just 5 miles away, Otis Reservoir is a stunning lake perfect for outdoor lovers. Enjoy swimming, kayaking, or simply relaxing on the beach while taking in the breathtaking scenery that creates a romantic backdrop for couples.
  • Ashintully Gardens: A mere 4 miles from The Berkshires, Ashintully Gardens features beautifully landscaped grounds ideal for family outings. Stroll through vibrant flora and enjoy the tranquil ambiance, making it a perfect spot for a leisurely day outdoors.

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 with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1000000000000005°C)Light RainMostlySlightly LowAverage
February24.6°F (-4.1000000000000005°C)Light RainMostlyAverageAverage
March32.5°F (0.3°C)Light RainMostlyAverageSlightly Low
April44.2°F (6.800000000000001°C)Light RainMostlyAverageSlightly 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 RainMostlySlightly 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.

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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.