The Berkshires Vacations 2025 from CA $581

The Berkshires flight + hotel packages

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

The Little Lion

per person

May 26 - May 30

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Albany (ALB)

Stay at this 3-star motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Art et Industrie and Lake Mansfield Park are located nearby.

Brookmere

Save 100% on your flight

per person

Jun. 15 - Jun. 22

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

Book a stay at this spa hotel in Saratoga Springs. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Saratoga Race Course and Saratoga Performing Arts Center are located nearby.

Club Wyndham Bentley Brook

per person

May 26 - May 30

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Albany (ALB)

Stay at this 3-star ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

Hampton Inn Albany-Wolf Road (Airport)

per person

Apr. 24 - May 1

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) 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.

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

per person

Apr. 24 - May 1

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Albany (ALB)

Book a stay at this business-friendly hotel in Clifton Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions The Edge Halfmoon and Clifton Park Ice Arena are located nearby.

Top The Berkshires hotels deals

Life House Berkshires

194 Pittsfield Rd, Lenox, MA

Free cancellation

Reserve now, pay when you stay

CA $139

CA $155 total

includes taxes & fees

7 Apr - 8 Apr

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

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

Free cancellation

Reserve now, pay when you stay

CA $171

CA $204 total

includes taxes & fees

26 Mar - 27 Mar

Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, 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

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA

Free cancellation

Reserve now, pay when you stay

CA $127

CA $141 total

includes taxes & fees

1 Apr - 2 Apr

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 Williams Inn

101 Spring Street, Williamstown, MA

Free cancellation

Reserve now, pay when you stay

CA $274

CA $306 total

includes taxes & fees

26 Mar - 27 Mar

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

190 Meadow Street, South Lee, MA

Free cancellation

CA $170

CA $210 total

includes taxes & fees

26 Mar - 27 Mar

Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.

Pool

Air conditioning

The Red Lion Inn

30 Main Street, Stockbridge, MA

Free cancellation

Reserve now, pay when you stay

CA $170

CA $254 total

includes taxes & fees

14 Apr - 15 Apr

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.

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

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.

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.

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 $581. 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.