The Berkshires Vacations from $733

Book a Hotel + Flight or Car together to unlock savings

Photo by Photo courtesy of Berkshire Visitors Bureau
  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Wilder House Berkshires
The Cornell Inn, Lenox & The Berkshires
The Dewey
The Ponds at Foxhollow
Beatrice by Avantstay Charming Catskills Escape
Don't see what you're looking for?
See all available trips from Columbus to The Berkshires
View all trips

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
$102 nightly
The price is $114 total per night from Aug 27 to Aug 28
$114 total
Aug 27 - Aug 28
Total includes taxes and fees
8.6/10 Excellent! (1,928 reviews)
"Nice and quiet also clean."

Reviewed on Aug 4, 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
$146 nightly
The price is $164 total per night from Aug 24 to Aug 25
$164 total
Aug 24 - Aug 25
Total includes taxes and fees
8.8/10 Excellent! (538 reviews)
"Great price for area with clean and spacious suites. Would be perfect if offered on site breakfast."

Reviewed on Aug 3, 2025

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $79 total per night from Aug 19 to Aug 20
$79 total
Aug 19 - Aug 20
Total includes taxes and fees
5.2/10 (761 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on Aug 2, 2025

FairBridge Inn Express
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.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.