It's hard not to unwind when you take a luxury vacation to Berkshire. From the stunning pastoral views to the variety of amenities, your vacation here is sure to be filled with bliss. Take a trip to the Tanglewood Music Center, home of the Boston Symphony Orchestra, where you can enjoy world class entertainment. Tour The Mount for a great glimpse into a stunning manor filled with history. Afterwards, unwind in your accommodations at Red Lion Inn. First established as a stage coach stop in 1773, the Red Lion Inn is one of the few American inns that has been in constant use. Their charming rooms are complete with 18th-century furniture and Sealy Elite Plush mattresses with Italian bedding. For a complete golfing and spa experience, stay with Cranwell Spa & Golf Resort. With an 18-hole championship golf course and a 35,000 square foot spa, you'll never be short of relaxation! Stay in Berkshire for a truly refreshing vacation.
Showing 1-13 of 13 Luxury Resorts
Head to Massachusetts and enjoy a boutique resort, The Porches Inn. Bringing together a little of the old with the new, the Porches Inn features... more
- Family
- Meetings
- Wedding
- Nature
- Romantic
- Pet Friendly
- Luxury
- Mountain
- Historical
- Bed & Breakfasts, Inns
Birchwood Inn offers a luxurious New England inn experience! Resting in Lenox, Massachusetts, this charming retreat lets you escape the hustle-bustle... more
- Family
- Wedding
- Nature
- Romantic
- Luxury
- Mountain
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
The Red Lion Inn brings together the historic with the new in the heart of the Massachusetts Berkshires. Here, you will fall for their charming rooms... more
- Family
- Nature
- Romantic
- Pet Friendly
- Luxury
- Mountain
- Historical
- Honeymoon
- Bed & Breakfasts, Inns
From its 18-hole championship golf course to 35,000 square foot luxury spa, Cranwell Spa & Golf Resort truly offers an elegant and spectacular... more
- Family
- Golf
- Meetings
- Wedding
- Nature
- Romantic
- Pet Friendly
- Luxury
- Historical
- Honeymoon
- Health
- Cabins, Cottages, and Chalets
- Holiday
- Spa
The Inn at Stockbridge is everything you're looking for in an exceptional Berkshires vacation. This luxurious retreat offers elegant accommodations... more
- Golf
- Wedding
- Nature
- Romantic
- Pet Friendly
- Luxury
- Historical
- Honeymoon
- Bed & Breakfasts, Inns
- Spa
Relax in spacious suites filled with designer fabrics and canopied beds. Enjoy a moment of peace and quiet in your private bath, fitted with a... more
- Family
- Golf
- Fishing
- Ski/Snowboard
- Luxury
The Hampton Terrace Bed & Breakfast Inn is one of the elite Berkshire inns. Completely renovated and restored, this famous inn features stunning... more
- Historical
- Holiday
- Luxury
- Romantic
- Bed & Breakfasts, Inns
The perfect marriage of the grandeur of a Florentine palazzo with elegance and comfort of the 21st century. On 22 acres overlooking the Berkshire... more
- Luxury
1896 House Luxury Inn is dedicated to creating an exceptional and unique lodging option in the Williamstown, Massachusetts area. With each suite... more
- Golf
- Historical
- Luxury
- Nature
- Romantic
With the beautiful Berkshires as your backdrop, a getaway at Canyon Ranch in Lenox is a luxury experience you won't soon forget. This premier health... more
- All-Inclusive
- Meetings
- Family
- Health
- Lake
- Luxury
- Nature
- Pet Friendly
- Spa
Dining is an experience unto its own in the Berkshires, which even boasts an annual festival to celebrate the foods that grace its much-heralded... more
- Historical
- Luxury
- Timeshare
From its stunning 125-year old architecture to its array of modern amenities, Kemble Inn redefines luxury. Relax on their spacious veranda overlooking... more
- Meetings
- Holiday
- Honeymoon
- Luxury
- Romantic
- Wedding
From double beds to king suites, Black Swan Inn offers luxury accommodations in the foothills of the Berkshire Mountains. Flat-screen televisions,... more
- Family
- Romantic
- Ski/Snowboard
- Luxury
- Mountain
- Lake
- Honeymoon