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Showing 31-45 of 66 Resorts and Lodges

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

Hampton Terrace Bed and Breakfast Inn

Lenox, Massachusetts, United States
96
Excellent
14 Reviews
$175

Bask in the Gilded Age during your stay at the Hampton Terrace Bed & Breakfast Inn. Step back – to an era of hope and prosperity. This historic inn has been renovated and restored to preserve its Gilded Age glory. Once the playground of the rich and famous (Vanderbilts and Carnegies), the Hampton Terrace Bed & Breakfast Inn is... more

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

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

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 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 Orchard Hotel

Williamstown, Massachusetts, United States

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

Gateways Inn & Restaurant

Lenox, Massachusetts, United States
85
Very Good
31 Reviews

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

The Garden Gables Inn

Lenox, Massachusetts, United States
97
Excellent
7 Reviews
$199

On the rolling hills of five beautiful acres, is the quaint and quiet Garden Gables Inn. Take a break from the hectic life that pulls relentlessly at you, and remember all the simple pleasures in life. Enjoy a refreshing dip in the swimming pool, spend the afternoon working those knots out at the spa or just relax on the porch with a good book or... more

Seven Hills Country Inn & Restaurant

Lenox, Massachusetts, United States
$151

An elegant country inn, and fine dining restaurant, located in the heart of the Berkshires.... more

The Morgan House Inn

Lee, Massachusetts, United States
76
Good
13 Reviews

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

Race Brook Lodge

Sheffield, Massachusetts, United States
$76

Race Brook Lodge proudly proclaims itself the Berkshires most interesting "chintz free" rustic mountain hideaway. The beautifully restored 200 year old New England timber peg barn sits at the base of the Taconic Range in Western Massachusetts. For outdoor lovers, hike to the Appalachian Trail, ski Butternut, canoe the Housatonic and more.... more

Showing 31-45 of 66 Resorts and Lodges

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