Enter your name and email to receive alerts when new vacation deals are added to any property in this region.
By clicking "Submit" you are agreeing to the
Terms of Service.
Alert successfully created!
Showing 16-30 of 65 Resorts and Lodges
Built in the grand era of the 1920's, the elegant Applegate is set amid towering pines and manicured lawns. Once inside the iron gate, the circular drive leads to the dramatic two-story, pillared port-cochere of this Georgian colonial. Applegate is all year for guests to enjoy Tanglewood and the cultural wonders of the Berkshires in warm weather... more
The Williamsville Inn in the Bershires has all the amenities an escape to the countryside needs--comfortable lodging, candlelit dining fireside, a cozy tavern, ten acres of towering pines and vegetable and flower gardens, a swimming pool and clay tennis court and even a wonderful swing hanging from an ancient elm.... more
The Old Inn on the Green & Gedney Farm are located in the Old Berkshire village of New Marlborough, now a National Historic District. Enjoy the tranquilty and dine in the only restaurant in the Berkshires rated 3 stars by The Boston Globe!... more
Soon to be listed on the National Register of Historic Buildings, the Federal House is located in the Berkshires close to summer music, drama and dance festivals. Golf and tennis privileges are available at the Stockbridge Country Club, two miles directly down Main Street and in the winter cross-country and downhill ski areas are nearby.... more
Chesapeake Inn of Lenox in the Berkshires is only one quarter mile from Tanglewood's East Gate and one mile from the center of Lenox. Rooms feature queen sized beds, private baths, central air conditioning, fresh cut flowers. Pampering personal service includes full breakfast, newspapers, after concert snacks. Heated 75' lap pool.... more
The 1896 House, nestled in Massachusetts' Berkshire Hills, offers its guests natural beauty as well as the cultural activities of the Berkshires. Built in 1896 as a milking barn, complete with bull pen, the house was turned into a famous restaurant in 1939 and continues its reputation seving for wonderful Yankee cuisine to this day.... more
Located in the heart of Williamstown, in the beautiful Berkshires of Western Massachusetts, the Williamstown Motel is just minutes from Williams College, Williamstown Theater Festival, Sterling and Francine Clark Art Institute, Williams College Museum of Art, MASS MoCA in North Adams, Mount Greylock State Reservation and Jiminy Peak Ski Resort, as... more
Located in the small, charming Massachusetts town of West Stockbridge, Shaker Mill Inn is a bed and breakfast that offers comfortable, spacious suite-style rooms. And, you guessed it -- breakfast with croissants, turnovers, ham and cheese biscuits, muffin tops, scones, breakfast bars, cinnamon-raisin-walnut buttermilk rolls, delicious quiches, tart... more
Brookside & Pondside Country Motel is an enchanting "retro" property on a brook and a pond. This bed and breakfast features a variety of polished and charming rooms, some featuring Jacuzzis, canopy beds, and parlor stoves. A full hot breakfast buffet is available to all guests, as well as a seasonal heated pool. The properties also offer... more
Barnside Luxury Inn is an enchanting three building property on a brook and pond, tucked away amongst forests and parks near Williamstown, Massachusetts. Boasting a total of six luxury suites, along with a full-country candlelight gourmet breakfast every morning. Each suite is designed to adopt a different "period" personality and is furnished with... more