The Berkshires Vacation Packages 2025 from $805

The Berkshires flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Landing Hotel at Rivers Casino & Resort

Stockade Historic District

per person

Jul 21 - Jul 25

found 9 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Albany (ALB)

This smoke-free hotel features a casino and 5 restaurants. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference center. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.

Lodges At Cresthaven

Save 100% on your flight

per person

Jul 21 - Jul 25

found 9 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Albany (ALB)

A private beach, a 24-hour gym, and a restaurant are all featured at this smoke-free lodge. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the seasonal outdoor pool, bar/lounge, and laundry facilities.

Brookmere

per person

Jul 21 - Jul 25

found 9 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Albany (ALB)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Surfside On The Lake

per person

Jul 21 - Jul 25

found 9 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Albany (ALB)

This hotel features a private beach and 2 restaurants. Dine at the beachfront restaurant and relax with sun loungers. Enjoy the a rooftop terrace and perks like free self parking.

Mohican Resort Motel

per person

Jul 21 - Jul 25

found 9 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Albany (ALB)

This motel features an indoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.

Top The Berkshires hotels deals

Life House Berkshires

194 Pittsfield Rd, Lenox, MA

$115

includes taxes & fees

$103 per night

May 1 - May 2

A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. Express check-in is provided and the front desk is staffed around-the-clock.

Pet friendly

Parking included

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

190 Meadow Street, South Lee, MA

Free Cancellation

Reserve now, pay when you stay

$134

includes taxes & fees

$120 per night

May 14 - May 15

This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.

Pool

Air conditioning

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

$120

includes taxes & fees

$107 per night

May 4 - May 5

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Hotel Downstreet, Ascend Hotel Collection

40 Main St, North Adams, MA

Free Cancellation

Reserve now, pay when you stay

$141

includes taxes & fees

$127 per night

May 1 - May 2

This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and perks like free self parking and free WiFi. A communal living room, express check-out, and luggage storage are also on offer.

Pool

Hot Tub

The Williams Inn

101 Spring Street, Williamstown, MA

$314

includes taxes & fees

$281 per night

May 29 - May 30

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking, a coffee shop, and a terrace are also offered.

Pet friendly

Parking included

The Red Lion Inn

30 Main Street, Stockbridge, MA

$211

includes taxes & fees

$189 per night

May 4 - May 5

This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Pool

Spa

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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

A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip

Tanglewood Music Center

5/5(150 reviews)

You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.

Hancock which includes signage and autumn leaves

Jiminy Peak Mountain Resort

4.5/5(98 reviews)

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.

Mount Greylock

4.5/5(91 reviews)

Explore the great outdoors at Mount Greylock and enjoy the mountain views during your trip to Adams. You can seek out the ski slopes while in the area.

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, as well as flights and hotels, starting from an impressive $805. With all that extra cash, you could purchase some cool tours or possibly add a couple of extra days to your exciting getaway.

Where can I get the best vacation package deals for The Berkshires?

Travelocity has endless ways to score an incredible The Berkshires package deal. Choose from 400 partner airlines and 1,000,000 properties around the globe and craft a vacation package that’s right for you. With so much choice, you have inspiration galore for your next big getaway.

Why should I purchase my The Berkshires vacation package via Travelocity?

Fantastic savings, an abundance of breathtaking destinations and a team of customer service experts available 24/7 — that’s why. And with our Price Match Guarantee, you can rest assured knowing that you’ll always get the best possible deal with Travelocity.

Will I save money on my The Berkshires car rental if I combine it with a hotel or flight?

Combining your bookings into a The Berkshires vacation package will save you some serious money. Book a flight and car; a flight, car and hotel; or a car and hotel. You won’t find a better way to discover the greater The Berkshires region than with your own set of wheels. You can also add experiences and activities to your Travelocity package.

Which airport is best for The Berkshires?

Bradley Intl. Airport (BDL) is a popular choice for many travelers to the region. But depending on your itinerary, Albany Intl. Airport (ALB) or Hartford, CT (HFD-Hartford - Brainard) could work better for you.

What is there to do in The Berkshires?

The Berkshires boasts hidden gems at every turn, but be sure you plan a visit to both Williams College and National Shrine of the Divine Mercy while you’re here. These landmarks are a must-see for visitors to the region.