The Berkshires Vacations 2025/2026 from CA $679

The Berkshires flight + hotel packages

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

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

CA $679

per person

Oct 23 - Oct 27

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Albany (ALB)

Stay at this 3.5-star 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 Tanglewood Music Center and Berkshire Theatre Festival are located nearby.

Prospect Berkshires

CA $1,160

per person

Oct 23 - Oct 27

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Albany (ALB)

Stay at this 3-star hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.

The Dewey

CA $1,553

per person

Oct 26 - Nov 1

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Albany (ALB)

Stay at this 3.5-star guesthouse in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.

The Cornell Inn, Lenox & The Berkshires

CA $1,449

per person

Oct 26 - Nov 1

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Albany (ALB)

Stay at this 3.5-star B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.

The Constance by the Lenox Collection

CA $1,589

per person

Oct 26 - Nov 1

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Albany (ALB)

Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Lenox Library 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 $120

CA $150 total

Sep 21 - Sep 22

includes taxes & fees

Stay at this 3-star 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.

Pool

Parking included

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Free cancellation

Reserve now, pay when you stay

CA $211

CA $266 total

Oct 1 - Oct 2

includes taxes & fees

Stay at this 3-star 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

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

190 Meadow Street, South Lee, MA

Free cancellation

Reserve now, pay when you stay

CA $161

CA $199 total

Sep 16 - Sep 17

includes taxes & fees

Pool

Air conditioning

Hotel Downstreet, an Ascend Collection Hotel

40 Main St, North Adams, MA

Free cancellation

Reserve now, pay when you stay

CA $211

CA $235 total

Sep 22 - Sep 23

includes taxes & fees

Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. 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.

Pool

Hot tub

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA

Free cancellation

Reserve now, pay when you stay

CA $128

CA $143 total

Sep 29 - Sep 30

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.

Breakfast included

Parking included

The Red Lion Inn

30 Main Street, Stockbridge, MA

Free cancellation

Reserve now, pay when you stay

CA $264

CA $357 total

Sep 17 - Sep 18

includes taxes & fees

Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition 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.

Hancock which includes signage and autumn leaves

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.

Mount Greylock

Explore the great outdoors at Mount Greylock and enjoy the mountain views during your trip to Adams. You can seek out the ski slopes while 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 $679. 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.