The Berkshires Vacations from $731

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Photo by Photo courtesy of Berkshire Visitors Bureau

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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.
Lodges At Cresthaven

Lodges At Cresthaven

Save 100% on your flight
$731
per person
Jan 7 - Jan 14
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.4/10 Exceptional! (643 reviews)
The Lodges at Cresthaven is truly a magical place. The grounds and property are expertly maintained with beautiful flowers and festive decorations. The suite are spacious and clean. The staff is friendly and helpful. This is my second time there and this suite was better than the first! I will return year after year!

Reviewed on Oct 23, 2026

The Perch Hotel

The Perch Hotel

Save 100% on your flight
$887
per person
Jan 8 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.6/10 Exceptional! (41 reviews)
The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

$2,686
per person
Jan 8 - Jan 11
found 11 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.8/10 Exceptional! (36 reviews)
Everything was amazing. Shawn was awesome. He greeted you when we came in. It's definitely experiences. All I can say we had a great time. A little quirky.Amazing history set on 200 acres closed down zoo

Reviewed on Sep 21, 2026

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

$2,092
per person
Jan 8 - Jan 11
found 11 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
No reviews
Historic & Secluded Estate on the Hudson River w/ Pool Sleeps 24 River House by Avantstay

Historic & Secluded Estate on the Hudson River w/ Pool Sleeps 24 River House by Avantstay

$2,961
per person
Jan 8 - Jan 11
found 11 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
No reviews
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Stay near popular The Berkshires attractions

A forested hillside with a clear path and a small building at the top.

Jiminy Peak Mountain Resort

8.8/10 (311 reviews)
Southern New England's largest ski resort transforms into a summer playground with thrilling attractions. Glide down 45 winter trails or ride the Mountain Coaster through Berkshire Mountain scenery.
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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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A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

Williams College

9.4/10 (534 reviews)
Williams College offers a prestigious liberal arts education amid the scenic Berkshire Mountains. Visitors can explore the renowned Williams College Museum of Art and attend public lectures in this intellectual haven.
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A calm river surrounded by autumn foliage.
Photo by Adnan Kakazai

Norman Rockwell Museum

9.4/10 (347 reviews)
This gallery houses the world's largest collection of Norman Rockwell's iconic American illustrations. Explore his relocated studio on the scenic Berkshire estate for insight into his creative process.
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A building with 'MASS MoCA' written on it, surrounded by greenery and hills.
Photo by Caminante

Massachusetts Museum of Contemporary Art

9.4/10 (246 reviews)
This converted factory houses one of America's largest contemporary art museums. Wander through MASS MoCA's vast industrial galleries to experience thought-provoking works that transcend artistic boundaries.
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Ski Butternut

9.0/10 (134 reviews)
Ski Butternut offers 22 diverse trails across 110 acres of terrain suitable for all skill levels. Morning visits reward skiers with freshly groomed slopes and the satisfaction of first tracks.
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National Shrine of the Divine Mercy

9.0/10 (83 reviews)
This serene sanctuary in the Berkshire Mountains is a center for Divine Mercy devotion inspired by Saint Faustina. Visitors can join the daily 3:00 PM Chaplet or walk contemplative trails.
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Lee Premium Outlets

8.2/10 (265 reviews)
You can find the perfect gifts to bring home at Lee Premium Outlets during your trip to Lee. Amble around the area's gardens or attend a sporting event.
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The Berkshires Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$109 nightly
$122 total
Nov 25 - Nov 26
Total with taxes and fees
9/10 Wonderful! (1,228 reviews)
"outside view,cleanness,large space"

Reviewed on Oct 25, 2026

Berkshire Mountain Lodge
Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
Fully refundable
$75 nightly
$84 total
Nov 22 - Nov 23
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
"The hotel was clean and pleasant. Staff members were courteous and helpful! Very satisfied with our stay and will consider a future stay here!"

Reviewed on Oct 24, 2026

Quality Inn Great Barrington
See all 1,090 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.

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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Frequently asked questions

What's included in a Berkshires vacation package?
A Berkshires vacation package in Lenox lets you combine flights, hotel stays, and rental cars. Most hotels in Lenox offer free breakfast, and many also provide airport shuttle service to and from Hartford, CT (BDL-Bradley Intl.).Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a The Berkshires vacation package?
When you bundle, you can save up to 30%*. To save money on a The Berkshires package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What is the best time to visit The Berkshires?
The peak season for a Berkshires vacation is generally from July through September, with August being the most popular month. This period sees the highest demand for travel to the region.
Which destinations should I consider for a Berkshires vacation?
When planning a Berkshires vacation, several towns offer distinct experiences and a good range of lodging options:
  • Great Barrington: A strong choice for those seeking adventure activities and outdoor pursuits, including skiing.
  • Lenox: Ideal for romantic getaways and cultural trips, with a focus on entertainment and family-friendly attractions.
  • Hancock: Primarily known for skiing and other outdoor and sports activities, making it a great base for active travelers.
  • Lee: Offers a mix of romantic appeal and family-friendly attractions, alongside various outdoor activities.
  • Pittsfield: Another excellent option for skiing enthusiasts, with plenty of adventure and outdoor activities.
Is The Berkshires better suited for a beach vacation or a cultural trip?
The Berkshires is primarily an outdoor and nature destination, known for its scenic views, adventure activities, and skiing. Travelers on a Berkshires vacation can enjoy activities like exploring Mount Greylock or hitting the slopes at Ski Butternut.Alongside its natural beauty, the region also offers a rich cultural experience. You can visit institutions like the Massachusetts Museum of Contemporary Art in North Adams, or catch a performance at Tanglewood Music Center in Lenox. The Norman Rockwell Museum in Lenox also provides a glimpse into American art and history.Overall, The Berkshires is best suited for those seeking outdoor adventures and scenic beauty, with a strong complement of cultural attractions to explore.
Which airport should I use for a Berkshires vacation?
For a Berkshires vacation, several major airports serve the wider region, requiring onward travel to your specific destination within The Berkshires. Top options include John F. Kennedy International Airport (JFK) and LaGuardia Airport (LGA) in New York, Logan International Airport (BOS) in Boston, and Bradley International Airport (BDL) in Hartford, Connecticut.
What are the top things to do in The Berkshires?
A Berkshires vacation is best explored from a base like Great Barrington, which offers a variety of outdoor and adventure activities:Browse and book things to do in The Berkshires on Expedia.
Can I change or cancel my The Berkshires vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking The Berkshires vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later The Berkshires vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your The Berkshires vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to The Berkshires?
To find last-minute vacation packages to The Berkshires, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on The Berkshires vacation packages?
Free cancellation on a The Berkshires vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a The Berkshires vacation as a package or separately?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your The Berkshires getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my The Berkshires vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.