The Berkshires Vacations 2026 from CA $992

The Berkshires flight + hotel packages

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

Berkshire Mountain Lodge

CA $992

per person

Jul 14 - Jul 17

found 15 hours ago

Roundtrip non-stop flight included

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

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 Wiltwyck

CA $1,685

per person

Aug 13 - Aug 19

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Albany (ALB)

Stay at this guesthouse in Kingston. Enjoy free WiFi, free parking, and Netflix. Popular attractions Senate House State Historic Site and Volunteer Fireman's Hall and Museum of Kingston are located nearby.

The Hideout Catskills Cottage

CA $2,394

per person

Aug 13 - Aug 19

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Albany (ALB)

Stay at this vacation home in Kingston. Enjoy free parking and a garden. Popular attractions Rosendale Trestle and Rosendale Public Library are located nearby.

Vacation Village in the Berkshires

CA $1,058

per person

Jul 15 - Jul 19

found 23 hours ago

Roundtrip non-stop flight included

Windsor (YQG) 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.

Berkshires Untold

CA $1,149

per person

Jul 14 - Jul 17

found 15 hours ago

Roundtrip non-stop flight included

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

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.

Top The Berkshires hotels deals

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free cancellation

Reserve now, pay when you stay

CA $168

CA $219 total

Jun 4 - Jun 5

includes taxes & fees

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

CA $165

CA $199 total

Jun 4 - Jun 5

includes taxes & fees

Pool

Parking included

Berkshires Untold

194 Pittsfield Rd Lenox MA

CA $148

CA $166 total

Jun 4 - Jun 5

includes taxes & fees

Pet-friendly

Parking included

The Yankee Inn

461 Pittsfield Rd Lenox MA

CA $146

CA $163 total

Jun 4 - Jun 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

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free cancellation

CA $128

CA $143 total

Jun 23 - Jun 24

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 Red Lion Inn

30 Main Street Stockbridge MA

CA $205

CA $291 total

Jun 9 - Jun 10

includes taxes & fees

Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.

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

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 quaint area.

Massachusetts Museum of Contemporary Art

You can spend time browsing the exhibits at Massachusetts Museum of Contemporary Art in North Adams. Take in the fascinating museums while you're in the area.

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 $992. 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.