Where to Stay in the Berkshires | Hotels & Inns

Planning a getaway to beautiful western Massachusetts this summer? Here are some of our favorite Berkshires hotels and inns to consider.

By Joe Bills

May 26 2022


Porches Inn | Favorite Berkshires Hotels

Photo Credit : Courtesy of Porches Inn
There are many reasons to visit the Berkshires, from gorgeous country views and fine restaurants to cultural gems such as Tanglewood, Mass MoCA, and Jacob’s Pillow. But where to stay in the Berkshires? There are a number of options at all budget levels, but here, in no particular order, are nine of our favorite Berkshires hotels, inns, and B&Bs.

10 Favorite Berkshires Hotels & Inns

The Porches Inn

The 47 guestrooms at the Porches Inn in North Adams are located in a cluster of beautifully converted Victorian row houses located adjacent to the Massachusetts Museum of Contemporary Art (Mass MoCA). The rooms feature whimsical retro decor but with all the modern comforts and technology. There is an indoor/outdoor pool, a bonfire pit, and nature trails to explore. If your visit is art-inspired, you’ll love the ArtCountry package, which includes tickets to not only Mass MoCA but also the Clark Art Institute, the Williams College Museum of Art, and Bennington Museum.
Gateways Inn | Favorite Berkshires Hotels
The Gateways Inn | Favorite Berkshires Hotels
Photo Credit : Chibi Moku

The Gateways Inn

The Gateways Inn in Lenox has a legacy of excellence, and a collection of Yankee “Best of New England” awards to match. Built as a summer escape for the family of Procter & Gamble heir Harvey Procter in 1912, the mansion has been extensively renovated and transformed into a truly memorable bed-and-breakfast inn. Just a mile and a half from Tanglewood, Gateways offers 11 rooms, including some with sleigh beds or fireplaces. There is plenty to do in the area, but if you choose to stay in, the Restaurant at the Gateways Inn features a seasonal menu that won’t disappoint, and a drink in the lounge is the perfect way to wind down the day. Named a 2017 Yankee Editors’ Pick for “Best Learning Escape” and 2016 Yankee Editors’ Pick for “Best Mansion.”

Seven Hills Inn

Surrounded by 27 acres of stunning lawns and gardens, this Gilded Age mansion in Lenox is noted for its lush landscape. From the antique furnishings and handcarved fireplaces to the leaded glass windows and eclectic art, Seven Hills Inn balances the celebration of original details with the luxury of modern comforts. The original 1700s farmhouse was enlarged and improved by a succession of owners, most notably Emily Meredith Read Spencer, a blue-blooded descendant of William Bradford. It has served as an inn since 1951 and has welcomed such Tanglewood luminaries as Leonard Bernstein, Beverly Sills, Seiji Ozawa, and Dave Brubeck. As it’s located next door to Edith Wharton’s historic estate, the Mount, and within easy distance of Tanglewood, Shakespeare & Company, and most of the area’s other highlights, you’ll be faced with some tough choices: Do you want to get out and experience, or stay in and relax? Named a 2015 Yankee Editors’ Pick for “Best Inn Landscape.”
Guest House at Field Farm
Guest House at Field Farm | Favorite Berkshires Hotels
Photo Credit : Kristin Teig

Guest House at Field Farm

The Guest House at Field Farm in Williamstown is truly a one-of-a-kind experience. The original house was built for modern art collectors Lawrence and Eleanor Bloedel in 1948, and the influence of the Bauhaus movement remains throughout the rooms, which are filled with modern art and furniture. Lose yourself in the sculpture gardens or feel free to wander farther afield, since the Guest House is a mere few miles from downtown Williamstown but also in the midst of more than 300 acres of conservation land, with miles of trails and sweeping views of Mount Greylock. Named a 2014 Yankee Editors’ Pick for “Best Retro Lodging,” the house also makes an appearance on our list of the best modern house museums in New England.
The Red Lion Inn
The Red Lion Inn | Favorite Berkshires Hotels
Photo Credit : Aimee Tucker

The Red Lion Inn

The Red Lion Inn, which is among the oldest hotels in the Berkshires, has been welcoming guests for more than 200 years. Located in the heart of Stockbridge, the Red Lion offers 125 eclectic guestrooms, as well as suites and “bed-and-breakfast” rooms. Nine guesthouses are also available. The outdoor pool is heated for year-round use, and the excellent on-site restaurants offer formal and casual dining as well as nightly entertainment.
Wheatleigh | Favorite Berkshires Hotels
Wheatleigh | Favorite Berkshires Hotels
Photo Credit : Courtesy of Wheatleigh


Wheatleigh was built in 1893 by tycoon Henry H. Cook as a wedding present for his daughter and her husband, a Spanish noble. Inspired by a 16th-century Italian palazzo, designed by Boston architects Peabody and Stearns, and built with materials and artisans direct from Italy, Wheatleigh is an extraordinary property—from the interior’s intricate carvings to the landscape design by Frederick Law Olmsted. Named a 2017 Yankee Editors’ Pick for “Best Romantic Getaway.”
Best Small-City Boutique Hotel | Hotel on North, Pittsfield
Hotel on North | Favorite Berkshires Hotels
Photo Credit : Martin Albert / Hotel on North

Hotel on North

Hotel on North in Pittsfield is anything but standard issue. Even the simplest things here offer pleasant little surprises — for instance, a birdcage elevator that’s been transformed into a two-person cocktail bar. The hotel’s historic buildings (formerly the home of legendary menswear and sporting goods emporium Besse-Clarke) have been lavishly updated, and the 45 guestrooms feature artistic touches. Named a 2016 Yankee Editors’ Pick for “Best Small-City Boutique Hotel.”
Blantyre | Favorite Berkshires Hotels
Blantyre | Favorite Berkshires Hotels
Photo Credit : Courtesy of Blantyre


Blantyre, a Scottish castle turned luxury resort in Lenox, is a Relais & Chateaux property and one of the most picturesque hotels in the Berkshires. Built for Robert Paterson starting in 1901, the house was modeled after his mother’s home in Blantyre, Scotland. The Tudor-style house fell into disrepair at one point, but you’d never know it now. Blantyre’s eight rooms, 10 suites, and three cottages are impeccable. Thousands of books shelved in the halls and rooms are available for guest use. During the winter months there’s an outdoor ice rink and horse-drawn carriage rides; in the summer the greens of the Cranwell Spa and Golf Resort are just steps away. Named a 2018 Yankee Editors’ Pick for “Best Luxury Escape.”

Black Swan Inn

Black Swan Inn in Lee is nestled in the foothills of the Berkshires on the shores of Lake Laurel. Whether you choose to rent a kayak or a pontoon boat and get out on the water, spend a day browsing the Main Street shops or the nearby outlet stores, or hit the hiking trails or ski slopes, Lee has plenty to offer. The Black Swan’s 52 spacious guestrooms are clean and well appointed. The on-site restaurant, Mint, serves classic Indian fare with a lake view. Named a 2016 Yankee Editors’ Pick for “Best Inn for Paddlers.”

Bascom Lodge

This sprawling 1930s stone-and-timber lodge at the 3,491-foot summit of Mount Greylock in Adams is a welcome sight to through-hikers on the Appalachian Trail. Yet it’s also accessible by road for a getaway at the top of Massachusetts. Fieldstone fireplaces and arts-and-crafts-style seating give common areas a rustic panache, while private bedrooms and group bunk-bed rooms are more simply furnished. Breakfast and dinner are available. Some summer nights feature live entertainment, but the stars shine nightly. Named a 2018 Yankee Editors’ Pick for “Best Wilderness Retreat.” Where are your favorite Berkshires hotels and inns? Let us know! This post was first published in 2017 and has been updated. 

SEE MORE: The Berkshires in Summer | My New EnglandA Weekend at Tanglewood in the Berkshires Things to Do in North Adams, Massachusetts | A Weekend of Art