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Showing 16-30 of 66 Resorts and Lodges

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

Berkshire Mountain House

Hancock, Massachusetts, United States

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

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

Card Lake Inn and Restaurant

Richmond, Massachusetts, United States
$76

The Card Lake Inn and Restaurant located in the eclectic arts community of West Stockbridge near Tanglewood. Built in 1805 as a stagecoach stop to rest the horses and provide lodging for the crew and passengers, the Inn's English style tavern has continued to attract visitors and neighbors like artist Norman Rockwell.... 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

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

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

Old Inn on the Green

New Marlborough, Massachusetts, United States
80
Very Good
27 Reviews
$151

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

Hampton Inn & Suites Berkshires-Lenox

Lenox, Massachusetts, United States
91
Excellent
236 Reviews

Vacation Village at Berkshires

Hancock, Massachusetts, United States
84
Very Good
767 Reviews

For years, the fortunate have flocked to the Berkshires Vacation Village timeshares to savor the region's incomparable complement of American history, natural beauty, sporting entertainment, and cultural enrichment. Soak in the charm of a bygone era while visiting the grounds and stately homes of legendary American figures. The scenic hills,... more

A B&B in the Berkshires

Richmond, Massachusetts, United States

The Ponds at Foxhollow

Lenox, Massachusetts, United States
83
Very Good
10 Reviews
$151

The Ponds at Foxhollow offers suites with fireplaces overlooking a scenic pond in the beautiful Berkshires. The grounds feature indoor and outdoor pools, outdoor tennis courts, basketball courts, a playground, rowboats and canoes for use on site and two-hundred acres to walk, hike, bike or cross country ski.... more

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

Black Swan Inn

Lee, Massachusetts, United States
$150

Located in the foothills of the Berkshire Mountains, the Black Swan Inn is at the heart of the action of Lee, Massachusetts. Whether you're passing through for the Tanglewood Music Festival, the Norman Rockwell Museum, Lee Premium Outlets or Jacob's Pillow Dance Festival you are sure to find many amenities and accommodations to keep coming back!... more

Showing 16-30 of 66 Resorts and Lodges

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