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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.
"The Untold is wonderfully posh and unique. The rooms are lovely, comfortable and nostalgic. The main seating area, bar, and restaurant have a feel that is texturally understandable to the senses that says "stay longer" to your nervous system."
"The location of this hotel is excellent. However, there was blood on the bathroom floor, stains on the sheets, and the fridge reeked of beer. When we asked the maintenance crew to give us five minutes to get out of the room, the cart was outside our door so we assumed that they would return and change the towels. They did not. The gentleman who checked me in was lovely; however, there was no one in the office when we checked out."
"This is very much like a quaint bed and breakfast rather than a hotel. My room was in a very old house modified to accommodate paid guests. Now, if that appeals to you, this is a great option. Unfortunately, it did not appeal to me, and the fault was mine--not the people who own and run this establishment. I should have done a much better job investigating before booking this property. I have nothing but good things to say about the hostess and other employees... I messed up, not them."
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.
All-inclusive The Berkshires holidays: everything you need to know
Can I book The Berkshires all-inclusive holidays with airfare and meals?
Use the all-inclusive filter to find amazing all-inclusive package holidays to The Berkshires, then just add on your flights with a few simple clicks. With everything from cocktails to car hire booked in one go, all you need to decide is whether you’ll be sipping a mojito or a margarita at sunset.
Why should I book a The Berkshires adults-only all-inclusive holiday?
If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to The Berkshires and you’re pretty much guaranteed a dreamy retreat. With those thoughtful grownup touches – beachside massage beds and live after-dinner music – an adults-only hotel levels up the sophistication on your holiday.
Can I book last minute all-inclusive holidays to The Berkshires?
Last-minute breaks are a great way to find very cheap all-inclusive holidays to The Berkshires. If you can be flexible with your holiday dates, browse our best The Berkshires deals and use the all-inclusive filter to add everything that makes your hols perfect.
Can I book a cheap all-inclusive The Berkshires trip?
There are some nifty little tricks to find pocket-friendly all-inclusive breaks in The Berkshires. Try hunting around for cheaper deals in the off season by playing with your dates. Or you could also choose an all-inclusive hotel or resort a little off the beaten track. We have some top value deals starting at – and they’re easy to find if you sort your results by price. Prices and availability are subject to change. Additional terms may apply.
What should I look for when booking a 5-star all-inclusive holiday to The Berkshires?
All-inclusive holidays are such a treat, but a 5-star all-inclusive is a whole other level of luxury. Think butlers waiting on your every whim, infinity pools with epic ocean views and unlimited spa-ing for holiday heaven on cloud nine.
What should I consider when booking a The Berkshires all-inclusive family holiday?
If you’re holidaying with tots in tow, book an all-inclusive The Berkshires package with all the kid-friendly amenities. The action-packed kids’ clubs, the slide-tastic water parks, the fussy-eater-friendly restaurants: we have a stack of deals specifically designed with kids in mind.
How can I find the best deals on all-inclusive holidays to The Berkshires in 2026/2027?
There are great all-inclusive deals galore in The Berkshires. Sort by price to see the cheapest places to stay, and consider travelling during the less popular months when there’s often more availability and better prices.
Can I book an all-inclusive The Berkshires package with free cancellation and/or flexible dates?
Flexibility is key to a stress-free holiday. Look for properties with free cancellation or book now, pay later options. Then, if your plans change, just login to make changes in a few clicks.
Why should I book an all-inclusive The Berkshires package holiday with Expedia?
With a huge range of all-inclusive The Berkshires trips on offer, Expedia is your go-to place to find and book your trip. It’s super easy … and it’s all here.