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Discover the most popular places to visit in The Berkshires
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.
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.
Photo by Caminante
Open 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.
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.
Photo by Adnan Kakazai
Open 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.
Photo by Caitlin Reese
Open Photo by Caitlin Reese
Mount Greylock
9.4/10 (180 reviews)
Massachusetts' highest peak rewards hikers with panoramic views stretching 90 miles on clear days. Explore the Appalachian Trail segment or stay overnight at the historic Bascom Lodge for a summit sunrise experience.
National Shrine of the Divine Mercy
9.0/10 (83 reviews)
This serene sanctuary in the Berkshire Mountains is a centre for Divine Mercy devotion inspired by Saint Faustina. Visitors can join the daily 3:00 PM Chaplet or walk contemplative trails.
Lee Premium Outlets
8.2/10 (265 reviews)
You can do some window-shopping at Lee Premium Outlets during your visit to Lee. Amble around the area's gardens or attend a sporting event.
Top Kid friendly The Berkshires Hotels
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
"Extremely friendly and helpful staff upon arrival. Provide great insights on local restaurant opportunities, and included a five star breakfast. Highly recommend!"
"It’s best to have a lakeside room, as sitting in the little porch can be quite peaceful. We met a new friend from England as a result.
Also, breakfast is included, which was not made clear."
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.
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.
How can I find the best family-friendly holidays in The Berkshires?
At Expedia, it’s super-easy to find family-friendly holidays in The Berkshires in our vast inventory. Use our handy filters to find hotels and resorts with the best reviews, most amenities and lowest price tags. You can also hunt out great flights and smashing deals on car hire, so you can book the whole shebang in one place.
Are there any cheap The Berkshires family holidays?
Avoid forking out for multiple hotel rooms by booking a villa or apartment with a kitchen and give your brood plenty of space and all the meals they love at a fraction of the cost. Find the most affordable family holidays by filtering your search by price. Generally, The Berkshires family getaways start at . Prices and availability are subject to change and additional terms may apply.
Can I book an all-inclusive The Berkshires family holiday package?
All-inclusive holidays can keep the costs down when you’re travelling as a family. Think unlimited mocktails for the little'uns and double doses of gin for the bigguns. Use our all-inclusive filter to see what’s available in The Berkshires and book the whole package in just a few clicks.
How can I book the best family activity holiday in The Berkshires?
Family holidays are all about spending quality time together, laughing, playing and bonding as you try new things. Pack your trip full of family activities they’ll love and make memories that’ll last a lifetime.
Can I find luxury family holidays in The Berkshires?
To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in The Berkshires by using our 5-star filter. To really travel in style, use the first-class filter to find the best flights, too.
How can I search for The Berkshires family holiday deals?
Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available The Berkshires family holiday deals. If your travel dates are flexible, play around to see if you can find cheaper options or more availability at different times.
Can I book a The Berkshires family vacation package with free cancellation and/or flexible dates?
Plans change, so booking a family holiday with free cancellation is a great way to ensure you don’t lose out if they do. Use the fully refundable and reserve now pay later filters to find flexibility. Make sure you always check terms and conditions, too.
Why should I book my The Berkshires family trip with Expedia?
Forget family fights and start thinking about family flights. Our huge selection of easy to browse family-friendly holidays means you can find and book your dream family trip to The Berkshires in no time.