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 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 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
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
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
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 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
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
- Bed & Breakfasts, Inns
For years, the fortunate have flocked to the Berkshires Vacation Village timeshares to savor the region's incomparable complement of American... more
- Historical
- Luxury
- Timeshare
Race Brook Lodge proudly proclaims itself the Berkshires most interesting "chintz free" rustic mountain hideaway. The beautifully restored 200 year... more
- Family
- Pet Friendly
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
Whether you're looking for a romantic getaway, a family vacation, or just a week with friends you'll find exactly what you need to make it a special... more
- Family
- Meetings
- Reunions
- Wedding
- Nature
- Romantic
- Ski/Snowboard
- Mountain
- Villas and Condos
Yankee Inn
Discover a charming country hotel that's still just minutes away from plenty of Berkshires attractions at the Yankee Inn. This cozy destination offers... more
- Family
- Romantic
- Ski/Snowboard