The Berkshires Vacations from $653

We make it simple to travel somewhere new, with The Berkshires packages starting from as little as $653. You’ll have the flexibility to bundle your favorite airlines, hotels and car rental. For the ultimate getaway, why not add a few tours and experiences to your itinerary?

Just imagine all the thrilling things you could do in The Berkshires with extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and extras into a The Berkshires vacation package. You have plenty of choice when you book with Expedia too. In fact, you can pick from more than 550 airlines and 1,000,000 properties around the world. Whether you’re vacationing with the family or embarking on a solo adventure, exploring The Berkshires is better with a package.

Hampton Inn Boston - Logan Airport and Boston Park Plaza know how to make their guests feel welcome in Great Barrington. If you also plan to explore Hancock, have a look at Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel. Both are top picks with travelers.

Travelers are normally able to browse international flights on Expedia up to a year in advance of departure. Booking last minute? With a stroke of luck, it’s still possible to purchase a cheaper ticket only weeks before your flight.

Flights, hotels and a cool car for all your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you’ve made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to organizing your The Berkshires trip, you’re in charge!

Booking all the parts of your trip together is a simple way to save. Combine car rentals, airfares and hotels into a tidy little package. But hotels aren’t your only option. Expedia has all kinds of properties, including vacation rentals such as beachside villas and serviced residences. You’ve got loads of choices!

Yes — that’s one of the best things about an Expedia package. You’re the boss! We have access to more than 550 airline partners across the globe, so you have options galore when putting together your The Berkshires escape.

Don’t stress if you’re rethinking your The Berkshires vacation package — it’s possible to cancel or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We totally understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you’re ready to make changes, we’re ready to help.