The Berkshires Vacations 2026 from CA $826

The Berkshires flight + hotel packages

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

Vacation Village in the Berkshires

CA $826

per person

Aug 31 - Sep 3

found 1 day ago

Roundtrip non-stop 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.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

CA $1,670

per person

Aug 23 - Aug 30

found 18 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) 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 helpful staff and the clean rooms in our reviews. Popular attractions Lake Mansfield Park and Housatonic River are located nearby.

The Landing Hotel at Rivers Casino Schenectady

Nothside

CA $1,067

per person

Aug 31 - Sep 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

Book a stay at this business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Schenectady Light Opera Performing Arts Center are located nearby.

Hilton Albany

Downtown Albany

CA $1,128

per person

Oct 3 - Oct 5

found 15 hours ago

Roundtrip flight included

Kelowna (YLW) to Albany (ALB)

Book a stay at this business-friendly hotel in Albany. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MVP Arena and Palace Theater are located nearby.

Super 8 by Wyndham Latham/Albany Airport

CA $973

per person

Oct 3 - Oct 5

found 15 hours ago

Roundtrip flight included

Kelowna (YLW) to Albany (ALB)

Book a stay at this business-friendly motel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

Top The Berkshires hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free cancellation

Reserve now, pay when you stay

CA $174

CA $210 total

Jul 21 - Jul 22

includes taxes & fees

Pool

Parking included

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free cancellation

CA $225

CA $252 total

Aug 16 - Aug 17

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 Massachusetts Museum of Contemporary Art and MCLA Gallery 51 are located nearby.

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free cancellation

CA $166

CA $185 total

Aug 9 - Aug 10

includes taxes & fees

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.

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $192

CA $214 total

Jul 22 - Jul 23

includes taxes & fees

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.

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free cancellation

Reserve now, pay when you stay

CA $187

CA $241 total

Aug 19 - Aug 20

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.

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $231

CA $258 total

Jul 23 - Jul 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.

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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.

Stay near popular The Berkshires attractions

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

Tanglewood Music Center

9.6/10 (457 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.

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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 $826. 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.