The Berkshires Vacations 2025 from CA $744

The Berkshires flight + hotel packages

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

Valley Craft Ales

per person

Feb. 17 - Feb. 21

just found

Roundtrip non-stop flight included

Toronto (YTO) 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

Feb. 7 - Feb. 14

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) 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.

Aspen At Manchester

per person

Feb. 7 - Feb. 14

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) 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 Dana L. Thompson Memorial Park and Lye Brook Falls are located nearby.

The Hotel Vervana at Bennington

per person

Feb. 17 - Feb. 21

just found

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

Book a stay at this ski hotel in Bennington. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Museum are located nearby.

Kimpton Taconic Hotel, an IHG Hotel

per person

Feb. 7 - Feb. 14

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Albany (ALB)

Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing 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 $167

CA $186 total

includes taxes & fees

5 Jan - 6 Jan 2025

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

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA

Free cancellation

Reserve now, pay when you stay

CA $139

CA $155 total

includes taxes & fees

29 Dec - 30 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 Guido's Marketplace and Bousquet Ski Area are located nearby.

The Red Lion Inn

30 Main Street, Stockbridge, MA

Free cancellation

Reserve now, pay when you stay

CA $185

CA $271 total

includes taxes & fees

1 Jan - 2 Jan 2025

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 Schantz Galleries and Mission House are located nearby.

Life House Berkshires

194 Pittsfield Rd, Lenox, MA

Free cancellation

Reserve now, pay when you stay

CA $127

CA $142 total

includes taxes & fees

1 Jan - 2 Jan 2025

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 Kennedy Park and Pleasant Valley Wilderness Sanctuary are located nearby.

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

One West Street, Pittsfield, MA

Free cancellation

CA $142

CA $159 total

includes taxes & fees

5 Jan - 6 Jan 2025

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.

Quality Inn

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

Free cancellation

Reserve now, pay when you stay

CA $121

CA $136 total

includes taxes & fees

29 Dec - 30 Dec

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.

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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.

Bousquet Ski Area

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. 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 $744. 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.