The Berkshires Vacations 2026/2026

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 $142

CA $174 total

Jan 4 - Jan 5, 2026

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

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free cancellation

CA $167

CA $187 total

Jan 8 - Jan 9, 2026

includes taxes & fees

Book a stay at this business-friendly 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

Free cancellation

Reserve now, pay when you stay

CA $285

CA $319 total

Jan 3 - Jan 4, 2026

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

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $127

CA $142 total

Jan 4 - Jan 5, 2026

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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Free cancellation

Reserve now, pay when you stay

CA $134

CA $150 total

Jan 2 - Jan 3, 2026

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

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free cancellation

Reserve now, pay when you stay

CA $135

CA $181 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

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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 . 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.