Please note that many establishments throughout New England have modified their hours and/or operations in response to COVID-19. Always check for the latest information before making travel plans.
With its scenic views, top cultural offerings, and thriving dining scene, the Berkshires are a fantastic vacation destination in every season. Planning a visit? Read on for the perfect resort, hotel, or inn for every budget.
And don’t miss the 2020 Yankee feature, “The Berkshires: An Insider’s Guide.”
Where to Stay in the Berkshires | A Guide for Every Budget
A Scottish castle turned luxury resort in Lenox, Massachusetts, Blantyre is a Relais & Châteaux property and one of the most picturesque hotels in the Berkshires. Built in 1901–1902 as a residence for a wealthy businessman named Robert Paterson, the Tudor-style house was modeled after Paterson’s mother’s home in Blantyre, Scotland. The property’s eight rooms, 10 suites, and three cottages are impeccable, and guests are welcome to peruse the thousands of books shelved in the halls and rooms. During the winter months, there’s an outdoor ice rink and horse-drawn carriage rides; in the summer, the greens of Cranwell Spa & Golf Resort are just steps away.
Treat yourself to a truly luxurious Berkshires experience at Canyon Ranch in Lenox. Its gorgeous surroundings and top-notch amenities (which recently earned it a spot on Travel + Leisure’s “Top 10 Destination Spas in the U.S.”) provide guests with every opportunity to rest, recharge, and reinvigorate with a rotation of fitness classes, spa treatments, and wellness programs that range from stress management to group photography hikes. All meals and many perks are included in the rate.
Located on 380 acres in Lenox, Cranwell has long been a top Berkshires vacation destination, and its next chapter is sure to continue the tradition. While currently undergoing renovations, Cranwell will reopen in the spring of 2020 as two new properties: the inclusive Miraval Berkshires and the more traditional Wyndhurst Manor & Club.
One of the oldest hotels in the Berkshires, the Red Lion Inn has been welcoming guests for more than 200 years. Located in the heart of Stockbridge, Massachusetts, the Red Lion offers 125 eclectic guest rooms, 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.
Enjoy a cozy B&B experience with all the perks of a modern hotel at this thoroughly updated 1836 Lenox property owned and designed by design guru and local resident Annie Selke. The eight colorful guest rooms each offer a unique bedding-to-furnishings Annie Selke design experience, and a full gourmet breakfast is included with every stay. Love the inn amenities? Pop into the Annie Selke shop across the street to stock up on the same soaps, lotions, rugs, bedding, and more.
The 47 guest rooms at this inn are located in a cluster of beautifully converted Victorian row houses next to the Massachusetts Museum of Contemporary Art (Mass MoCA) in North Adams. 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.
This boutique hotel in Pittsfield, Massachusetts, 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 guest rooms feature artistic touches.
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 hand-carved 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 descendant of Plymouth Colony governor 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 everything, or stay in and relax?
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, the Gateways Inn offers 11 rooms, including some with fireplaces. There is plenty to do in the area, but if you choose to stay in, the on-site restaurant has a seasonal menu that won’t disappoint, and a drink in the lounge is the perfect way to wind down the day.
Road-trippers, families, and retro enthusiasts flock to this updated 1960s motel at the base of Monument Mountain in Great Barrington, Massachusetts, for a sleek and stylish motor lodge experience that’s fit for the 21st century. All 16 guest rooms (there’s also a one-bedroom suite) come with free Wi-Fi, an in-room fridge, and a complimentary locally sourced continental breakfast. Additional perks include a cozy lobby pellet stove, an outdoor fire pit, and use of the year-round, heated outdoor pool and hot tub at the nearby Red Lion Inn. Traveling with a furry friend? All well-behaved dogs are welcome, with no breed or weight restrictions.
This post was first published in 2020 and has been updated.