The Berkshires Vacations 2026/2026 from CA $1,388

The Berkshires flight + hotel packages

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

The Palmer House Resort, an Ascend Collection Hotel

CA $1,388

per person

Jan 18 - Jan 24

found 8 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

Book a stay at this golf hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Gander Gallery and Lye Brook Falls are located nearby.

The Manchester View

CA $1,965

per person

Jan 18 - Jan 24

found 8 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

Stay at this hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park are located nearby.

The Equinox Golf Resort & Spa

Manchester Village Historic District

CA $1,819

per person

Jan 18 - Jan 24

found 8 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.

Hill Farm Inn

CA $2,613

per person

Jan 18 - Jan 24

found 8 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

Stay at this B&B in Arlington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Equinox and Norman Rockwell Exhibition are located nearby.

Aspen At Manchester

CA $1,519

per person

Jan 18 - Jan 24

found 8 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

Stay at this hotel in Manchester Center. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park are located nearby.

Top The Berkshires hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

CA $143

CA $175 total

Dec 18 - Dec 19

includes taxes & fees

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.

Pool

Parking included

The Williams Inn

101 Spring Street Williamstown MA

Free cancellation

Reserve now, pay when you stay

CA $258

CA $289 total

Dec 21 - Dec 22

includes taxes & fees

Book a stay at this 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 $129

CA $144 total

Dec 20 - Dec 21

includes taxes & fees

Book a stay at this 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

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $130

CA $145 total

Dec 18 - Dec 19

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 Guido's Marketplace and Bousquet Ski Area are located nearby.

Pool

Hot tub

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free cancellation

Reserve now, pay when you stay

CA $136

CA $182 total

Jan 11 - Jan 12, 2026

includes taxes & fees

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 Guido's Marketplace and Herman Melville's Arrowhead are located nearby.

Pool

Hot tub

The Red Lion Inn

30 Main Street Stockbridge MA

CA $192

CA $276 total

Jan 14 - Jan 15, 2026

includes taxes & fees

Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Schantz Galleries and Mission House 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

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.

Tanglewood Music Center

5/5(6 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.

Bousquet Ski Area

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this family-friendly 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 $1,388. 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.