7 Cool Places to Stay

Book a room at these unique hotels, where retro style meets modern comfort.

“Take a drive through the Berkshires, and you’ll see mid-century roadside motor inns and hotels reimagined for modern travelers as boutique-style lodging with a nostalgic twist,” stated Lindsey Schmid, SVP of Tourism and Marketing of 1Berkshire, “From single-story motels nestled into a natural setting like Tourists to a re-envisioned former Holiday Inn near museums and outdoor adventures, these properties have everything you want in an unforgettable Berkshire getaway!”

Here are just a few of the possibilities:

Hotel Downstreet. Photo by Corey Favino.

Hotel Downstreet, North Adams

Along with a retro-modern vibe paying homage to its origins as a chain hotel built in the late ’60s, the guestrooms at Hotel Downstreet are comfy, the indoor pool is heated, and your pet is welcome! The Main Street location puts you close to shops, restaurants, and MASS MoCA.

Blue Vista Motor Lodge, Florida

Blue Vista Motor Lodge is a 17-room gem at the highest point on the scenic Mohawk Trail. Go hiking, explore local history, or discover world-class art at The Clark and MASS MoCA. End your day with a relaxing soak in the hot tub (weather permitting).

Williamstown Motel, Williamstown

A popular choice for visitors to Williams College and the Clark, the Williamstown Motel is walking distance to shops like ROAM: A Xtina Parks Gallery, restaurants, and a movie theater. Park your car at the door to your guestroom, unpack, and head out. A short drive takes you to MASS MoCA and Jiminy Peak.

Black Swan Inn, Lee-Lenox

Lakeside rooms (and dining next door at MINT) are only part of the appeal of Black Swan Inn. You’re close to golf courses, theaters, museums, or the Premium Outlets. Plus, guests enjoy access to a nearby town beach and kayak rentals (seasonal). It’s also in a central location for grabbing a coffee or dinner in downtown Lee, Lenox, and Stockbridge.

Berkshire Lakeside Lodge. Photo by Diana Mott Scarbo

Berkshire Lakeside Lodge, Becket

Berkshire Lakeside’s proximity to the Appalachian Trail and October Mountain State Forest makes this a good bet for hikers. Guests can rent canoes and kayaks to paddle on Greenwater Pond (seasonal) and have access to snowmobile trails in winter. Don’t miss the nearby Dream Away Lodge for dinner and live music.

The Little Lion, Great Barrington

Originally opened as a roadside motor lodge in the ’60s, The Little Lion is perfectly located near Berkshire attractions. Guests can enjoy the amenities at its sister property, The Red Lion Inn (including a year-round heated outdoor pool). Downtown Great Barrington is a few minutes away by car.

Monument Mountain Motel, Great Barrington

Coming in on the more budget side, the Monument Mountain Motel is a good choice for families. You’re a short drive to hiking, downtown Great Barrington, and Ski Butternut. There are two craft brew pubs, pizza, and a good breakfast spot within a mile.

Born in an era when families piled into the station wagon with map in hand and adventure in mind, these modernized vintage-style motels are a taste of living in simpler times. Each one has a story to tell. Come make your own, in the Berkshires!

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