The Berkshires Vacations 2025/2026 from CA $483

The Berkshires flight + hotel packages

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

The Clocktower Hotel at Century House, Ascend Hotel Collection

per person

Oct 20 - Oct 23

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Albany (ALB)

Book a stay at this business-friendly hotel in Cohoes. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Colonie Center Mall and Latham Farms 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 $119

CA $148 total

Aug 25 - Aug 26

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

Hotel Downstreet, Ascend Hotel Collection

40 Main St, North Adams, MA

Free cancellation

Reserve now, pay when you stay

CA $234

CA $261 total

Aug 3 - Aug 4

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

The Williams Inn

101 Spring Street, Williamstown, MA

CA $310

CA $347 total

Aug 14 - Aug 15

includes taxes & fees

Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Williams College Schow Science Library and Denison Park are located nearby.

Pet-friendly

Parking included

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street, Pittsfield, MA

Free cancellation

CA $177

CA $198 total

Aug 17 - Aug 18

includes taxes & fees

Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.

Pool

Pet-friendly

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA

Free cancellation

Reserve now, pay when you stay

CA $186

CA $207 total

Aug 17 - Aug 18

includes taxes & fees

Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Tracy Brook Wildlife Sanctuary are located nearby.

Breakfast included

Pet-friendly

FairBridge Inn Express

16 Cheshire Road, Pittsfield, MA

Free cancellation

Reserve now, pay when you stay

CA $98

CA $109 total

Jul 30 - Jul 31

includes taxes & fees

Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking and Crane Museum of Papermaking are located nearby.

Parking included

Free WiFi

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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 family-friendly 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 $483. 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.