Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Discover the most popular places to visit in The Berkshires
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.
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.
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.
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.
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.
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.
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.
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.
"This review is for the hotel. I stayed two nights (September 18 and September 19). Room #2. I am wondering if the sheets and the comforter were laundered before my arrival. The body smell from them was unbearable. Also all lights (the floor lamp and two lamps on the night stands) did not work. I know this is an inexpensive hotel (actually, not that inexpensive after all) but these things are absolutely necessary at any place where people stay."
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 do I book the best The Berkshires beach vacation packages?
Life’s a beach when you dive into our brilliant The Berkshires beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.
How can I find cheap beach vacations in The Berkshires?
A rental steps from the shore creates an amazingly affordable The Berkshires beach vacation. Seaside sojourns during low season start from . Prices and availability are subject to change. Additional terms may apply.
How can I book the best family beach vacations in The Berkshires?
With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.
How do I find a The Berkshires beachfront vacation?
Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.
Can I book a package including a The Berkshires vacation beach house rental?
Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.
Can I find The Berkshires beach vacation deals?
Sort your search results by deals to delight in amazing The Berkshires beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.
Can I book a The Berkshires beach trip with free cancellation and/or flexible dates?
Just like the The Berkshires tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.
Why should I book my The Berkshires beach vacation with Expedia?
Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in The Berkshires. (OK, maybe not that last part.)