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
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
- Family
- Nature
- Romantic
- Historical
- Honeymoon
- Bed & Breakfasts, Inns
Cranwell Spa & Golf Resort lies in the Berkshire Hills overlooking 380 picturesque acres. For your stay choose from 105 luxurious rooms with... more
- Family
- Golf
- Meetings
- Wedding
- Nature
- Romantic
- Pet Friendly
- Luxury
- Historical
- Honeymoon
- Health
- Cabins, Cottages, and Chalets
- Holiday
- Spa
The historic town of North Adams, Massachusetts is a unique destination for travelers of all kinds. Here, you will find charming 19th-century... more
- Family
- Meetings
- Wedding
- Nature
- Romantic
- Pet Friendly
- Luxury
- Mountain
- Historical
- Bed & Breakfasts, Inns
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
- Family
- Wedding
- Nature
- Romantic
- Luxury
- Mountain
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
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
- Golf
- Wedding
- Nature
- Romantic
- Pet Friendly
- Luxury
- Historical
- Honeymoon
- Bed & Breakfasts, Inns
- Spa
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
- Family
- Reunions
- Nature
- Romantic
- Ski/Snowboard
- Historical
- Boutique
- Holiday
- Bed & Breakfasts, Inns
For a relaxing and elegant Massachusetts vacation, look no further than the beautiful Lanesboro Country Inn. Surrounded by the stunning peaks of the... more
- Family
- Nature
- Romantic
- Pet Friendly
- Cabins, Cottages, and Chalets
- Holiday
- Bed & Breakfasts, Inns
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
- Family
- Nature
- Romantic
- Pet Friendly
- Luxury
- Mountain
- Historical
- Honeymoon
- Bed & Breakfasts, Inns
At Northside Motel you can enjoy a relaxing and fun Williamstown vacation that doesn't break the bank. Their affordable accommodations feature cable... more
The 1896 House, nestled in Massachusetts' Berkshire Hills, offers its guests natural beauty as well as the cultural activities of the Berkshires.... more
- Bed & Breakfasts, Inns
Located in the heart of the Berkshires, luxurious Devonfield is world in itself. For the enjoyment of its guests, Devonfield features a heated... more
- Bed & Breakfasts, Inns
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... more
- Reunions
- Wedding
- Romantic
- Ecotourism
- Historical
- Spa
- Bed & Breakfasts, Inns
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... more
- Family
- Romantic
- Ski/Snowboard
- Luxury
- Mountain
- Lake
- Honeymoon
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... more
- Bed & Breakfasts, Inns