The Berkshires Vacations 2024/2025 from CA $1,141

The Berkshires flight + hotel packages

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

Valley Craft Ales

per person

Jan. 13 - Jan. 18

found 11 hours ago

Roundtrip flight included

Calgary (YYC) to Albany (ALB)

Stay at this lodge in Wilmington. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions South Main Street and Jim McGrath Gallery and Studio are located nearby.

The Equinox Golf Resort & Spa

Save 100% on your flight

per person

Jan. 10 - Jan. 17

found 11 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Albany (ALB)

Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, a full-service spa, and 4 restaurants. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.

Hampton Inn Bennington

per person

Dec. 24 - Dec. 30

found 10 hours ago

Roundtrip flight included

Calgary (YYC) to Albany (ALB)

Book a stay at this business-friendly hotel in Bennington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Bennington Battle Monument and Old First Congregational Church are located nearby.

Wilburton Inn

per person

Jan. 10 - Jan. 17

found 11 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Albany (ALB)

Stay at this 3.5-star golf hotel in Manchester. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Museum of Creative Process and Hildene are located nearby.

Weathervane Motel

per person

Jan. 10 - Jan. 17

found 11 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Albany (ALB)

Stay at this motel in Manchester Center. Enjoy free WiFi, daily housekeeping, and satellite TV channels. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hildene and Equinox Preservation Trust are located nearby.

Top The Berkshires hotels deals

Hotel Downstreet

40 Main St, North Adams, MA

Free cancellation

Reserve now, pay when you stay

CA $162

CA $181 total

includes taxes & fees

8 Dec - 9 Dec

Stay at this 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 Massachusetts Museum of Contemporary Art and Studio 21 South are located nearby.

Pool

Hot tub

Life House Berkshires

194 Pittsfield Rd, Lenox, MA

Free cancellation

Reserve now, pay when you stay

CA $167

CA $187 total

includes taxes & fees

25 Nov - 26 Nov

Stay at this 3.5-star 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.

Pet-friendly

Parking included

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA

Free cancellation

Reserve now, pay when you stay

CA $131

CA $146 total

includes taxes & fees

1 Dec - 2 Dec

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

The Red Lion Inn

30 Main Street, Stockbridge, MA

Free cancellation

Reserve now, pay when you stay

CA $203

CA $289 total

includes taxes & fees

1 Dec - 2 Dec

Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. 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

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

Free cancellation

Reserve now, pay when you stay

CA $236

CA $273 total

includes taxes & fees

25 Nov - 26 Nov

Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

Pool

Kitchen

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

One West Street, Pittsfield, MA

Free cancellation

CA $132

CA $148 total

includes taxes & fees

30 Nov - 1 Dec

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

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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 family-friendly 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.

Norman Rockwell Museum

4.5/5(6 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint 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 $1,141. 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.