The Berkshires Vacations 2026 from CA $731

The Berkshires flight + hotel packages

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

Quality Inn Great Barrington

CA $731

per person

Aug 4 - Aug 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Albany (ALB)

Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.

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

CA $991

per person

Aug 4 - Aug 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Albany (ALB)

Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.

Vacation Village in the Berkshires

CA $749

per person

Aug 4 - Aug 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Albany (ALB)

Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

Hotel On North

CA $1,064

per person

Aug 4 - Aug 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Albany (ALB)

Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Lichtenstein Center for the Arts are located nearby.

The Yankee Inn

CA $1,129

per person

Aug 4 - Aug 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Albany (ALB)

Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

Top The Berkshires hotels deals

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free cancellation

CA $240

CA $268 total

Jul 12 - Jul 13

includes taxes & fees

Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MCLA Gallery 51 and North Adams Center are located nearby.

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free cancellation

Reserve now, pay when you stay

CA $172

CA $224 total

Jun 25 - Jun 26

includes taxes & fees

Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $180

CA $201 total

Jun 22 - Jun 23

includes taxes & fees

Pool

Hot tub

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free cancellation

Reserve now, pay when you stay

CA $158

CA $191 total

Jun 21 - Jun 22

includes taxes & fees

Pool

Parking included

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free cancellation

CA $147

CA $164 total

Jun 22 - Jun 23

includes taxes & fees

Breakfast included

Parking included

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $193

CA $215 total

Jun 23 - Jun 24

includes taxes & fees

Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.

Pet-friendly

Parking included

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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 wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

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.

Wide paths in the middle pf a forest shows the ski trails on the mountains in the summer

Jiminy Peak Mountain Resort

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

Williams College

Take a campus tour or just explore the area of Williams College, during your travels in Williamstown. In the area, take in the fascinating museums and mountain views.

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 CA $731. 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.