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You can certainly hear music in the mountains of the Berkshires region of Massachusetts! Home to the Tanglewood music venue and the annual Tanglewood Music and Jazz Festivals, relax to the melodies of the famous Boston Symphony Orchestra as well an array of world-renowned guest performers. Even if you think Tanglewood is all the art one region can handle, the Berkshires still offers other countless cultural institutions! The Norman Rockwell Museum in Stockbridge holds the largest collection of paintings by famed 20th-century Americana painter, Norman Rockwell. The annual Williamstown and Berkshire Theatre Festivals are the perfect places to see some of the world’s most popular actors practice their craft! The cultural opportunities in the Berkshire are endless!

Showing 1-15 of 59 Resorts and Lodges

Red Lion Inn

Stockbridge, Massachusetts, United States
$113
1-866-452-8654

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... more

Resort features:
  • Family
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Mountain
  • Historical
  • Honeymoon
  • Bed & Breakfasts, Inns

The Porches Inn

North Adams, Massachusetts, United States
$252
tel:+1-877-410-0514

The historic town of North Adams, Massachusetts is a unique destination for travelers of all kinds. Here, you will find charming 19th-century... more

Resort features:
  • Family
  • Meetings
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Mountain
  • Historical
  • Bed & Breakfasts, Inns

Cranwell Spa & Golf Resort

Lenox, Massachusetts, United States
$195
1-866-920-6347

Cranwell Spa & Golf Resort lies in the Berkshire Hills overlooking 380 picturesque acres. For your stay choose from 105 luxurious rooms with... more

Resort features:
  • Family
  • Golf
  • Meetings
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Historical
  • Honeymoon
  • Health
  • Cabins, Cottages, and Chalets
  • Holiday
  • Spa

Birchwood Inn

Lenox, Massachusetts, United States
$209
1-800-524-1646

Birchwood Inn brings together the charm of the past with the modern comforts of the present. This beautiful Massachusetts getaway is the perfect place... more

Resort features:
  • Family
  • Wedding
  • Nature
  • Romantic
  • Luxury
  • Mountain
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns

The Lanesborough Country Inn

Lanesborough, Massachusetts, United States
$69
1-866-836-8659

For a relaxing and elegant Massachusetts vacation, look no further than the beautiful Lanesboro Country Inn. Surrounded by the stunning peaks of the... more

Resort features:
  • Family
  • Nature
  • Romantic
  • Pet Friendly
  • Cabins, Cottages, and Chalets
  • Holiday
  • Bed & Breakfasts, Inns

The Cornell Inn Lenox

Lenox, Massachusetts, United States
$135
1-413-637-4800

The Cornell Inn Lenox offers peaceful Berkshire vacations with the historic charm of New England. This unique bed and breakfast is composed of three... more

Resort features:
  • Family
  • Reunions
  • Nature
  • Romantic
  • Ski/Snowboard
  • Historical
  • Boutique
  • Holiday
  • Bed & Breakfasts, Inns

The Inn at Stockbridge

Stockbridge, Massachusetts, United States
$150
1-888-466-7865

The air chills, evergreen trees grow heavy with fresh snow, and ice skates replace fishing poles. The Inn at Stockbridge brings guests closer to a... more

Resort features:
  • Family
  • Golf
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Honeymoon
  • Bed & Breakfasts, Inns

Brook Farm Inn

Lenox, Massachusetts, United States
$185
1 (413) 637-3013

The stunning Berkshires of Massachusetts are an incredible destination for any kind of vacation. Stay at the beautiful Brook Farm inn and bask in the... more

Resort features:
  • Family
  • Nature
  • Romantic
  • Historical
  • Honeymoon
  • Bed & Breakfasts, Inns

Northside Motel

Williamstown, Massachusetts, United States
$59
1-413-458-8107

At Northside Motel you can enjoy a relaxing and fun Williamstown vacation that doesn't break the bank. Their affordable accommodations feature cable... more

Williamstown Motel

Williamstown, Massachusetts, United States
$99
1-413-458-5202

Located in the heart of Williamstown, in the beautiful Berkshires of Western Massachusetts, the Williamstown Motel is just minutes from Williams... more

Shaker Mill Inn

West Stockbridge, Massachusetts, United States
$109
1-877-385-2484

Located in the small, charming Massachusetts town of West Stockbridge, Shaker Mill Inn is a bed and breakfast that offers comfortable, spacious... more

Resort features:
  • Honeymoon
  • Romantic
  • Ski/Snowboard

1896 House Luxury Inn

Williamstown, Massachusetts, United States
$179
1-413-458-1896

Barnside Luxury Inn is an enchanting three building property on a brook and pond, tucked away amongst forests and parks near Williamstown,... more

Resort features:
  • Golf
  • Historical
  • Luxury
  • Nature
  • Romantic

Rodeway Inn Lee

Lee, Massachusetts, United States
Resort features:
  • Bed & Breakfasts, Inns

Harbour House Inn

Cheshire, Massachusetts, United States
Resort features:
  • Bed & Breakfasts, Inns

Berkshire Mountain House

Hancock, Massachusetts, United States
Resort features:
  • Bed & Breakfasts, Inns

Showing 1-15 of 59 Resorts and Lodges

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