Save up to NZ$2,400 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 centre for Divine Mercy devotion inspired by Saint Faustina. Visitors can join the daily 3:00 PM Chaplet or walk contemplative trails.
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 to find luxurious holiday packages in The Berkshires?
How to find a luxury holiday in The Berkshires?
Whether you fancy heading off on an unforgettable spa break or relaxing on an all-inclusive vacation, finding your perfect 2026 luxury escape The Berkshires couldn’t be easier. Use Expedia’s filters to find luxury escapes The Berkshires hotels and luxury holiday rentals with the amenities you need to make your holiday extra special.
How to book a luxury holiday in The Berkshires with Expedia?
Once you’ve identified your ideal luxury holiday The Berkshires you simply need to enter your travel dates to view your travel and accommodation options. You can select from luxury holiday rentals to luxury hotels. Use the filters to find luxury escapes The Berkshires deals around your selected dates and you could save money too.
Are luxury holidays in The Berkshires worth the cost?
Memories are priceless so splashing out on luxury getaways to The Berkshires in 2026 can be well worth the extra expense. That said, there are some great value luxury escapes The Berkshires deals available if you’re prepared to book a holiday out of season. Consider booking villas or luxury holiday homes in The Berkshires for a group or larger family holiday to keep costs down.
How do I choose the perfect luxury holiday package for The Berkshires?
Make sure you think carefully about what you want from your luxury holiday in The Berkshires before you book. If you’re taking the kids, click on the “family-friendly” filter to find hotels with facilities they’ll love—along with a pool bar and sauna for the adults to enjoy.
Where can I find excellent deals on luxury holidays in The Berkshires?
Luxury doesn’t have to cost the earth. If you’re looking for discount luxury escapes The Berkshires deals, then Expedia can help. Whether you’re after cost-effective luxury weekend getaways to The Berkshires or a longer trip with luxury hire car, use the filters to access some of the best deals available.
How to find luxury spa The Berkshires holiday packages?
Expedia can help you discover some of the most luxurious spa hotels to fit your budget, taste, and dates. You can compare prices and read reviews before deciding. It’s also often possible to get a luxury holiday The Berkshires with free cancellation too, so you can book with confidence.
How to discover last-minute luxury holiday deals to The Berkshires with Expedia.
While booking ahead is a good way to seal in some great value deals, it’s also possible to access top-notch last-minute luxury escapes to The Berkshires. Simply enter your dates to see what’s on offer, and if you can be flexible about flights and hotels, so much the better for your pocket.
How to find luxury pet-friendly The Berkshires holiday packages?
If you don’t want to leave your pet at home, no problem. It doesn’t mean you have to miss out on luxury facilities. Use the “pet-friendly” filter to find luxury escapes The Berkshires hotels that will welcome your furry friend.
How to find great luxury beach holiday packages in The Berkshires?
To discover some of the most luxurious beach lodgings available, tick the “all-inclusive” and “sea view” filters. You’ll be able to select from a big selection of luxury escape The Berkshires hotels and apartments with direct access to beaches.
Why book luxury holiday packages in The Berkshires with Expedia?
Expedia’s handy travel filters can help you search through a huge number of options and book a luxury escape The Berkshires you’ll never forget. From rooms with a view to resorts with top-rated golf courses, you can customise your vacation and find one that ticks all your boxes.