Want travel alerts for this area?

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!

Go to Map View

Filters

Avg. Daily Rate
Resort Type
Activities
Amenities

Berkshire Articles

Showing 31-45 of 65 Resorts and Lodges

Applegate Inn

Lee, Massachusetts, United States
91
Excellent
10 Reviews
$151

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

Thornewood Inn & Restaurant

Great Barrington, Massachusetts, United States
81
Very Good
32 Reviews
$76

The Thornewood Inn, located in the heart of the beautiful Berkshire Hills, is the perfect place to vacation in any season. Conveniently situated at the base of Monument Mountain on five acres, the Inn is adjoined by a state forest and offers walking trails that double as cross country ski trails in winter when mother nature cooperates.... more

Red Lion Inn

Stockbridge, Massachusetts, United States
83
Very Good
285 Reviews
$76

Established as a stage coach stop in 1773 and rebuilt in 1897, The Red Lion Inn is one of the few remaining American inns in continuous use since the 18th century. As immortalized in Norman Rockwell's painting Main Street, Stockbridge, the Inn epitomizes New England tradition. When you step inside The Red Lion Inn, you enter a world full of... more

Kemble Inn

Lenox, Massachusetts, United States
87
Excellent
51 Reviews
$200

Four seasons of relaxation and excitement awaits for you at the beautiful Kemble Inn. This Berkshires destination combines the stunning architecture of a 125-year-old Gilded Age mansion with completely modern amenities and furnishings for a one-of-a-kind vacation experience. You'll fall in love with the charming mountain vista scenery, the spacious... more

A B&B in the Berkshires

Richmond, Massachusetts, United States

Jericho Valley Inn

Williamstown, Massachusetts, United States
78
Good
32 Reviews
$76

The Jericho Valley Inn is located on 350 pristine acres in the beautiful Berkshire Mountains of western Massachusetts. Enjoy the rich cultural offerings in and around Tanglewood or take advantage of Jericho Valley's special ski and golf packages.... more

The Yankee Suites Extended Stay

Pittsfield, Massachusetts, United States
82
Very Good
27 Reviews

The 1896 House

Williamstown, Massachusetts, United States
$76

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

The Williams Inn

Williamstown, Massachusetts, United States

The Orchards Hotel

Williamstown, Massachusetts, United States
83
Very Good
188 Reviews

Lanesboro Country Inn

Lanesborough, Massachusetts, United States
$69

The Lanesboro Country Inn is a wonderfully intimate, centrally located cozy retreat in the heart of the Berkshires. Featuring brand new , individual log cabins, it provides spacious accommodations to help you unwind. Come relax, discover, and enjoy everything the Berkshires have to offer.... more

Gedney Farm

New Marlborough, Massachusetts, United States
$250

Gedney Farm was built in the turn of the century and modeled after the Normandy barns of nineteenth century France. Paired with modern amenities, this old meets new world lodge has sixteen exquisitely decorated rooms to create a quite and peaceful getaway. Whether you're looking for a romantic weekend for two, or a family stay you can find all the... more

Chesapeake Inn

Lenox, Massachusetts, United States
$151

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

Federal House Inn

Lee, Massachusetts, United States
94
Excellent
92 Reviews
$76

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

Brookside & Pondside Country Motel

Williamstown, Massachusetts, United States
$69

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

Showing 31-45 of 65 Resorts and Lodges

statsstats