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
At Northside Motel you can enjoy a relaxing and fun Williamstown vacation that doesn't break the bank. Their affordable accommodations feature cable... more
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
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
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
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 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
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
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
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
- Bed & Breakfasts, Inns
The Rookwood Inn is a restored fairy tale Victorian bed and breakfast in the charming village of Lenox. Peace, seclusion and relaxation are exactly... more
- Meetings
- Family
- Pet Friendly
- Romantic
- Wedding
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
For over 200 years the Village Inn has offered hospitality and lodging to Berkshire travelers. With their close proximity to Tanglewood, summer home... more
- Meetings
- Historical
- Nature
The Williams Inn
- Bed & Breakfasts, Inns
Located in the small, charming Massachusetts town of West Stockbridge, Shaker Mill Inn is a bed and breakfast that offers comfortable, spacious... more
- Honeymoon
- Romantic
- Ski/Snowboard