Berkshire, Massachusetts, Hotels

by T.L. Chancellor

Berkshire, Massachusetts, is a small town located in the heart of the Berkshires, which is a well-known region of Massachusetts that draws tourists year-round. The region is considered a cultural hub for art, antiques, music and the outdoors. Its popularity has prompted a wealth of accommodations in the area. Hotels include the area’s only five-star lodging and a local chain with three unique accommodation options.


The Blantyre, located in Lenox, is one of the most honored in the Berkshires and is just 15 miles from the town of Berkshire. It has a five-star rating from Forbes Travel Guide and it was voted the No. 1 small hotel by readers of Conde Nast Traveler magazine. The Blantyre began as a country estate in the late 1800s and is now a year-around destination for travelers who enjoy the luxury the hotel has to offer. Both the buildings and furnishings are done in the English style, and those staying in the hotel’s main house have easy access to the Blantyre’s music room and private dining areas. You can reserve a cottage or the Carriage House if you prefer to be on your own. Dining is an event, as guests for dinner can indulge in pre-meal champagne and canapés in the terrace area. The hotel has its own wine cellar with more than 19,000 bottles and awards from Wine Spectator magazine. The spa features body, hand and feet treatments, along with a hot tub.

New England History

The Red Lion in Stockbridge is a great place to go for a historical perspective on the Berkshires. The Red Lion has hosted New England travelers since the 1800s, making it one of the oldest hotels in the region. In fact, it is a charter member of Historical Hotels of America. The Red Lion features 108 rooms, suites and cottages, all of which are individually decorated and feature antiques and Colonial pewter. Dining is both casual and formal and features contemporary American cuisine with a menu that changes each season. For guests in the winter, they can take advantage of the Inn’s indoor pool -- heated at 80 degrees year around -- and hot tub. The Red Lion features entertainment on a nightly basis at the Lion’s Den Pub. Local performers are the norm, but the pub has hosted nationally-known performers like James Taylor during its history.

The Local Chain

The Berkshire Inns chain offers three different lodging options in the Berkshires. The Yankee Inn, the largest of the three is located in Lenox and offers a free continental breakfast, indoor and outdoor pools, a hot tub, access to a nearby day spa and fireplaces in some rooms. The Yankee Suites in Pittsfield is an extended-stay type of hotel and offers full kitchens, dining area, living area and outdoor deck in all suites. The Chambery Inn, located in Lee, was built as a schoolhouse in 1885 and is now a French country-inspired inn with canopy beds, fireplaces and room-delivered breakfast.

The Crowne

The Crowne Plaza in Pittsfield will appeal to travelers who trust a national name brand rather than a locally-owned hotel. Recently renovated, the hotel’s location for those who intend to drive to Boston or New York City, explore the Appalachian Trail or just browse through the art and antiques of the Berkshires. The Crowne Plaza has both standard rooms and suites, some of which are either poolside or provide views of the mountains. Along with an indoor pool, restaurant and fitness center, guests with pets will like the hotel. Service dogs may stay free, while other pets can stay for a small fee.

About the Author

T.L Chancellor has more than 12 years of newspaper reporting and editing experience. She has written extensively about education, business and city government. She has also worked at a public relations firm, focusing on environmental issues with clients.