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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

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

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

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

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 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

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

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

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

Rodeway Inn Lee

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

Wyndham Vacation Resorts - Bentley Brook

Hancock, Massachusetts, United States
$129
413-738-8600

See the mountainside suspended from a chairlift above Jiminy Peak Mountain and discover an unparalleled vacation destination at Wyndham Bentley Brook!... more

Resort features:
  • Historical
  • Mountain
  • Ski/Snowboard
  • Villas and Condos

Crowne Plaza Hotel Pittsfield – Berkshires

Pittsfield, Massachusetts, United States

Applegate Inn

Lee, Massachusetts, United States
$151
(800) 691-9012

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... more

Resort features:
  • Bed & Breakfasts, Inns

Thornewood Inn & Restaurant

Great Barrington, Massachusetts, United States
$76
(800)854-1008

The Thornewood Inn, located in the heart of the beautiful Berkshire Hills, is the perfect place to vacation in any season. Conveniently situated at... more

Resort features:
  • Bed & Breakfasts, Inns

Devonfield Inn

Lee, Massachusetts, United States
$151
1.413.243.3298

Located in the heart of the Berkshires, luxurious Devonfield is world in itself. For the enjoyment of its guests, Devonfield features a heated... more

Resort features:
  • Bed & Breakfasts, Inns

Showing 1-15 of 59 Resorts and Lodges

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