The Berkshires Vacations 2025/2026 from CA $752

The Berkshires flight + hotel packages

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

Vacation Village in the Berkshires

CA $752

per person

Oct 31 - Nov 3

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

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.

The Equinox Golf Resort & Spa

CA $905

per person

Oct 31 - Nov 3

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.

The Landing Hotel at Rivers Casino & Resort

Stockade Historic District

CA $903

per person

Nov 21 - Nov 23

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

Stay at this 4-star 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 Scene One Movieland are located nearby.

Hilton Garden Inn Albany Airport

CA $924

per person

Nov 21 - Nov 23

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

Stay at this 3-star business-friendly hotel in Albany. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

Hampton Inn Albany-Wolf Road (Airport)

CA $901

per person

Nov 21 - Nov 23

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

Book a stay at this business-friendly hotel in Albany. 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 $120

CA $149 total

Sep 22 - Sep 23

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.

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Free cancellation

Reserve now, pay when you stay

CA $210

CA $265 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.

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

190 Meadow Street, South Lee, MA

Free cancellation

CA $178

CA $218 total

Sep 17 - Sep 18

includes taxes & fees

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.

Pool

Air conditioning

Hotel Downstreet, an Ascend Collection Hotel

40 Main St, North Adams, MA

Free cancellation

Reserve now, pay when you stay

CA $210

CA $234 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.

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 30 - Oct 1

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

Free cancellation

Reserve now, pay when you stay

CA $263

CA $356 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.

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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 $752. 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.