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

Showing 31-45 of 66 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

Chambery Inn

Lee, Massachusetts, United States
94
Excellent
183 Reviews

Make your Massachusetts getaway extraordinary at Chambery Inn. In this nineteenth century parochial school turned country inn, you will find nine exceptional rooms French-inspired design and little touches of luxury that will help you relax. Start your day with a charming breakfast basket, delivered right to your door, before venturing out into the... more

Ramada Limited & Suites Pittsfield

Pittsfield, Massachusetts, United States

Gateways Inn & Restaurant

Lenox, Massachusetts, United States
85
Very Good
31 Reviews

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

The Village Inn

Lenox, Massachusetts, United States
$122

For over 200 years the Village Inn has offered hospitality and lodging to Berkshire travelers. With their close proximity to Tanglewood, summer home of the Boston Symphony, good music is a major part of life at the Inn. Classical recordings accompany gourmet dining, and a grand piano in the Common Room is frequently played by guests and guest... more

Jiminy Peak Mountain Resort

Hancock, Massachusetts, United States
78
Good
289 Reviews
$109

Whether you're looking for a romantic getaway, a family vacation, or just a week with friends you'll find exactly what you need to make it a special trip at Jiminy Peak. Standing at the base of the mountain is the 105-suite Country Inn, offering you luxurious rooms with plush beds and fully-equipped kitchenettes. The Country Inn is more than just a... more

The Orchards Hotel

Williamstown, Massachusetts, United States
83
Very Good
188 Reviews

The Inn at Stockbridge

Pittsfield, Massachusetts, United States
$151

Set back from the road on twelve secluded acres just one mile from downtown Stockbridge in the Berkshires is the Inn at Stockbridge. The Inn is a Georgian-style mansion with large white pillars built as a private residence in 1906. Filled with antiques, the Inn remains an elegant, comfortable base from which to explore the Berkshires' cultural and... more

Wheatleigh

Stockbridge, Massachusetts, United States
96
Excellent
14 Reviews
$251

The perfect marriage of the grandeur of a Florentine palazzo with elegance and comfort of the 21st century. On 22 acres overlooking the Berkshire Mountains and lake, Wheatleigh is two and a half hours by car from New York and Boston, with easy access by private plane. Built in 1893, Wheatleigh has just completed a four-year renovation to create one... 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

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

Canyon Ranch in Lenox

Lenox, Massachusetts, United States
93
Excellent
9 Reviews
$1,130

Since 1979, Canyon Ranch has been empowering people to live healthier, longer, more joyful lives through fitness, nutrition, stress management and integrative wellness. At Canyon Ranch health resort in Lenox, located within walking distance of the lovely town of Lenox and close to upstate New York, experience the all-inclusive luxury spa vacation... more

Blantyre

Lenox, Massachusetts, United States
$251

"America's Consummate Estate Sanctuary" -Andrew Harper's Hideaway Report Open May 14th through November 7th, 1999... more

Windflower Inn

Great Barrington, Massachusetts, United States
$151

The Windflower is a classic New England inn, located on a Berkshire County estate dating back to the 1850's. A full breakfast is served daily along with tea and homemade cookies in the afternoon. All rooms have privatebath, AC and many have a working fireplace. The Inn has its own pool and is directly across from a public golf course. The area... more

Showing 31-45 of 66 Resorts and Lodges

statsstats