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Showing 31-45 of 66 Resorts and Lodges

Berkshire Mountain Lodge

Pittsfield, Massachusetts, United States

You can find spectacular accommodations at Vacation Village properties across the country, but for a real treat head to Pittsfield, Massachusetts, and the Berkshire Mountain Lodge. Featuring 146 one-bedroom condominiums with great amenities like fully-appointed kitchens, individual living and dining areas, and two HD televisions, you will feel... more

Devonfield Inn

Lee, Massachusetts, United States
92
Excellent
39 Reviews
$151

Located in the heart of the Berkshires, luxurious Devonfield is world in itself. For the enjoyment of its guests, Devonfield features a heated swimming pool, tennis court, bicycles, and acres of lawn perfect for cross country skiers. Its convenient location offers access to the Berkshire Theatre Festival, Tanglewood, Jacob's Pillow, and fine... more

Summerhill Farm

Lenox, Massachusetts, United States
$76

Summerhill Farm in Lenox, Massachusetts has been a working family farm since pioneer days. For 150 years, descendants of the original owner have farmed the land and extended the house and barns. The barn and lower farmhouse are now a small horse farm. Located near the cultural activities of the Bershires, Summerhill Farm offers gracious lodging.... 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

The Orchard Hotel

Williamstown, Massachusetts, United States

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

The Morgan House Inn

Lee, Massachusetts, United States
76
Good
13 Reviews

White Horse Inn

Pittsfield, Massachusetts, United States
90
Excellent
46 Reviews

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

The Porches Inn

Clarksburg, Massachusetts, United States
90
Excellent
186 Reviews

1896 House Luxury Inn

Williamstown, Massachusetts, United States
$179

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

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

Wyndham Vacation Resorts - Bentley Brook

Hancock, Massachusetts, United States
90
Excellent
118 Reviews
$129

See the mountainside suspended from a chairlift above Jiminy Peak Mountain and discover an unparalleled vacation destination at Wyndham Bentley Brook! This premier Hancock, MA vacation resort is located at the foot of the ski slopes of Jiminy Peak Mountain Resort. After a full day of skiing, snowboarding, hiking and partaking in other seasonal... more

The Williams Inn

Williamstown, Massachusetts, United States

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

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