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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 Cornell Inn, Lenox & The Berkshires
Hotel Brookmere & Arbor Spa
Hampton Inn Albany-Wolf Road (Airport)
Saratoga Casino Hotel
Hilton Garden Inn Albany Airport
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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
$126 nightly
The price is $141 total per night from Jan 12 to Jan 13
$141 total
Jan 12 - Jan 13
Total with taxes and fees
8.6/10 Excellent! (2,202 reviews)
Clean rooms, chimney did not work

Reviewed on Jan 4, 2026

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
Fully refundable
$125 nightly
The price is $140 total per night from Feb 2 to Feb 3
$140 total
Feb 2 - Feb 3
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
friendly accommodating staff

Reviewed on Jan 1, 2026

Hotel Downstreet, an Ascend Collection Hotel
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$98 nightly
The price is $109 total per night from Jan 23 to Jan 24
$109 total
Jan 23 - Jan 24
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN

Reviewed on Jan 4, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.

Find the Best The Berkshires Vacation Packages

Things to do near The Berkshires

The Berkshires offers a perfect blend of outdoor adventure and stunning scenery, making it an ideal vacation spot. Visitors can enjoy skiing at local resorts, explore scenic hiking trails, and take leisurely drives through picturesque landscapes. Additionally, there are various recreational opportunities and nearby attractions that enhance the experience, ensuring a memorable getaway in this beautiful region of Massachusetts.

Shopping

The Berkshires offer a delightful shopping experience. Visit Lee Premium Outlets, 10 miles away, for a variety of brands and family-friendly vibes. Explore the Berkshire Mountain Country Store, 11 miles distant, for unique gifts, and browse The Bookstore, 15 miles away, for a charming selection of literature.

Recreation

Experience the artistry of dance at Jacob's Pillow, where culture and romance flourish. Unwind at Goose Pond Reservation, a serene spot perfect for relaxation and rejuvenation. Enjoy family-friendly entertainment at the Mahaiwe Performing Arts Center, where captivating performances create lasting memories.

Adventure

Hit the slopes at Ski Butternut, located 9 miles from The Berkshires, offering thrilling runs and a vibrant ski atmosphere. For a scenic hike, explore the Housatonic River Walk, 11 miles away, immersing yourself in nature's beauty. Otis Ridge, only 3 miles distant, promises exciting skiing adventures.

Nightlife

The Berkshires offer a vibrant nightlife with venues like the Mahaiwe Performing Arts Center for live performances and the Barrington Stage Company for theater. Enjoy a cozy atmosphere at The Marketplace Café for drinks, or head to Club Helsinki for music and dancing, making for an unforgettable evening.

*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 and cultural experiences, featuring historic houses, beautiful lakes, and inviting libraries. Visitors can explore attractions like the Berkshire Museum and the scenic Berkshire Mountains, catering to those seeking adventure and relaxation amid stunning landscapes. Whether you're interested in history or nature, The Berkshires promises a memorable getaway for every type of traveler.

  • National Shrine of the Divine Mercy: Located 12 miles from The Berkshires, this serene shrine offers a tranquil atmosphere for reflection and prayer. Its stunning architecture and beautiful grounds invite visitors to experience the spiritual ambiance and connect with the culture of devotion.
  • Otis Reservoir: Just 5 miles away, Otis Reservoir is a perfect spot for outdoor lovers. Enjoy the picturesque beach and breathtaking scenery, ideal for romantic picnics or adventurous water activities like kayaking and fishing, all set against a backdrop of natural beauty.
  • Ashintully Gardens: Situated 4 miles from The Berkshires, this enchanting botanical garden features lush landscapes and vibrant flora. It's a family-friendly destination where visitors can stroll through beautifully designed gardens, making it a perfect spot for relaxation and bonding.

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.

The Berkshires Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)

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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.