The Berkshires Vacations 2026 from CA $575

The Berkshires flight + hotel packages

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

Vacation Village in the Berkshires

CA $575

per person

Sep 19 - Sep 21

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Albany (ALB)

Book a stay at this family-friendly aparthotel 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.

Brook Bound Inn

CA $1,361

per person

Oct 14 - Oct 18

found 14 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.

The White House Inn

CA $1,613

per person

Oct 14 - Oct 18

found 14 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

Stay at this hotel in Wilmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.

The Brooks Motel

CA $1,204

per person

Sep 4 - Sep 7

found 24 hours ago

Roundtrip non-stop flight included

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

Stay at this motel in Hillsdale. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Roe Jan Brewing Co. and Catamount Aerial Adventure Park are located nearby.

Hotel Vervana, Trademark Collection by Wyndham

CA $1,181

per person

Oct 14 - Oct 18

found 14 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

Book a stay at this ski hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Museum 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 $130

CA $161 total

Aug 13 - Aug 14

includes taxes & fees

Pool

Parking included

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free cancellation

CA $209

CA $233 total

Sep 1 - Sep 2

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

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free cancellation

Reserve now, pay when you stay

CA $140

CA $188 total

Aug 31 - Sep 1

includes taxes & fees

Book a stay at this golf aparthotel 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

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free cancellation

CA $130

CA $145 total

Sep 1 - Sep 2

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 $199

CA $222 total

Aug 4 - Aug 5

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.

Pool

Hot tub

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $206

CA $230 total

Sep 1 - Sep 2

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.

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 $575. 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.