Deals on vacations and trips to The Berkshires

Save when you book The Berkshires, MA package deals

Choose two or more items and save on your trip:

The Berkshires flight + hotel vacation packages

Surfside On The Lake
The Springs Motel
Amsterdam Castle
Nordick's Inn
Park Manor Hotel

Top The Berkshires hotels deals

Don't see what you're looking for?
See all available properties in The Berkshires
View all properties
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.

Popular places to visit

The Berkshires Vacations

The highlands known as The Berkshires are situated in Western Massachusetts and Connecticut and are some of the best-known tourist attractions in the region. With impressive mountains, scenic hills, and beautiful autumn foliage, experiencing a vacation in The Berkshires is one of the best ways to get to know one of the Northeast's most beautiful regions.

Major Attractions

After you've checked into your hotel in the Berkshires, dive right into your vacation with a visit to the Massachusetts Museum of Contemporary Art. Located in a converted factory in nearby North Adams, this unique space is one of the largest and most notable spaces for contemporary visual and performing arts in the country. This museum's 100,000 square feet of space hosts a rotation of exhibitions from artists from around the world. When you're done exploring the Berkshires' ample art scene, get intimate with nature in the area's extensive wild spaces. One of the standouts is the Mt. Everett State Reservation, a 1,356-acre natural space in the southwest corner of the state. In addition to climbing to this mountain's summit, Mt. Everett offers its visitors picnicking and the chance to explore the 90-mile Appalachian Trail that wanders through the site.

Recurring Festivals and Events

Tourists planning their Berkshires vacations should prepare for the annual festivals in the region. For instance, the nearby Bay State Winter Games showcases some of winter's best sports, including ice skating, skiing, and more. Summer's annual Berkshire Arts Festival in July displays some of the works of some of the region's most innovative visual artists and allows visitors the chance to purchase many works.

It's easy to get Berkshires vacation packages and even rental cars in the Berkshires through Travelocity. When you book through us, you can take advantage of our Travelocity Price Guarantee: If you find a better deal through a competitor, we'll match their price and refund you the difference.

Frequently asked questions

How much are vacation packages to The Berkshires?
Travelocity has great package deals to The Berkshires, including hotels and flights, starting from as low as $618. With the cash you save, you could book some popular tours or maybe even tack on a few extra nights to your vacation.
Where can I get the best vacation package deals for The Berkshires?
No matter your travel style, Travelocity can help you get an unbeatable The Berkshires package deal. All you need to do is mix and match from our 400 air carriers and 1,000,000 worldwide properties.
Why should I book my The Berkshires vacation package via Travelocity?
Whether you’re planning a month-long vacation or a last-minute escape, we have many tempting destinations to choose from at an affordable price. And on top of that, we provide round-the-clock support, quality service and a Price Match Guarantee. Save yourself the effort and time and lock in your dream vacation now.
Can I save money on my The Berkshires car rental if I combine it with hotels and flights?
You sure can with our The Berkshires vacation packages. With one of these, there are loads of ways to stretch your vacation budget further. Combine any two or more car, hotel, flight and tour bookings and watch the savings start to pile up. With a rental car, all the key sights in and around The Berkshires are within your reach.
What is the best time of year to go to The Berkshires?
If you really want to wander wisely, is the perfect time to do it. That’s when hotel rates are at their cheapest. By way of comparison, prices are at their highest around . are the most popular months to vacation in The Berkshires, so expect big lines at top attractions. Want to avoid high season? You’ll find fewer crowds in .
Which airport is best for The Berkshires?
There are three main hubs for anyone heading to and from The Berkshires — Bradley Intl. Airport (BDL), Albany Intl. Airport (ALB) and Hartford, CT (HFD-Hartford - Brainard).
Can I go on vacation to The Berkshires at this time?
Our team has the local know-how to ensure your travel dreams come true, so before booking a ticket to The Berkshires, look over our Covid-19 Travel Advisor. Here you’ll find all the current info about quarantine policies, travel restrictions and other useful advice.