The Berkshires Vacations 2026 from CA $729

The Berkshires flight + hotel packages

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

Vacation Village in the Berkshires

CA $729

per person

Oct 7 - Oct 12

found 20 hours ago

Roundtrip flight included

Toronto (YTO) 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.

Saratoga Casino Hotel

CA $1,673

per person

Sep 6 - Sep 12

found 1 day ago

Roundtrip flight included

St. John's (YYT) to Albany (ALB)

Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Casino and Raceway and Saratoga Racetrack are located nearby.

Quality Inn Lee - Lenox South

CA $936

per person

Oct 7 - Oct 12

found 20 hours ago

Roundtrip flight included

Toronto (YTO) to Albany (ALB)

Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Lee Library are located nearby.

The Yankee Inn

CA $1,020

per person

Oct 7 - Oct 12

found 20 hours ago

Roundtrip flight included

Toronto (YTO) 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.

Quality Inn Great Barrington

CA $919

per person

Oct 7 - Oct 12

found 20 hours ago

Roundtrip flight included

Toronto (YTO) 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.

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 $157

CA $191 total

Aug 11 - Aug 12

includes taxes & fees

Pool

Parking included

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

CA $227

CA $253 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.

Pool

Hot tub

Quality Inn Great Barrington

372 Main Street Great Barrington MA

CA $167

CA $186 total

Aug 12 - Aug 13

includes taxes & fees

Breakfast included

Parking included

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $216

CA $241 total

Jul 23 - Jul 24

includes taxes & fees

Pool

Hot tub

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

CA $177

CA $229 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.

Pool

Hot tub

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $232

CA $259 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.

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.

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.

See properties

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 $729. 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.