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 lies in the Berkshire Hills overlooking 380 picturesque acres. For your stay choose from 105 luxurious rooms with... more
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- Golf
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- Romantic
- Pet Friendly
- Luxury
- Historical
- Honeymoon
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- 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 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
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 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
Surrounded by the beautiful Berkshire Mountains of Massachusetts awaits a charming destination for your next vacation. The Maple Terrace Motel offers... more
- Romantic
- Pet Friendly
- Mountain
- Honeymoon
Best Western Plus Berkshire Hills Inn & Suites
The Lanesboro Country Inn is a wonderfully intimate, centrally located cozy retreat in the heart of the Berkshires. Featuring brand new , individual... more
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
Berkshire Mountain Lodge
You can find spectacular accommodations at Vacation Village properties across the country, but for a real treat head to Pittsfield, Massachusetts, and... more