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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

Birchwood Inn

Lenox, Massachusetts, United States
$209
1-844-934-1851

Birchwood Inn offers a luxurious New England inn experience! Resting in Lenox, Massachusetts, this charming retreat lets you escape the hustle-bustle... more

Resort features:
  • Family
  • Wedding
  • Nature
  • Romantic
  • Luxury
  • Mountain
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns

The Inn at Stockbridge

Stockbridge, Massachusetts, United States
$150
1-888-466-7865

The Inn at Stockbridge is everything you're looking for in an exceptional Berkshires vacation. This luxurious retreat offers elegant accommodations... more

Resort features:
  • Golf
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Historical
  • Honeymoon
  • Bed & Breakfasts, Inns
  • Spa

Red Lion Inn

Stockbridge, Massachusetts, United States
$113
413-298-5545

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

Resort features:
  • Family
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Mountain
  • Historical
  • Honeymoon
  • Bed & Breakfasts, Inns

The Porches Inn

North Adams, Massachusetts, United States
$252
413.664.0400

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

Resort features:
  • Family
  • Meetings
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Mountain
  • Historical
  • Bed & Breakfasts, Inns

Cranwell Spa & Golf Resort

Lenox, Massachusetts, United States
$195
1-800-272-6935

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

Resort features:
  • Family
  • Golf
  • Meetings
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Historical
  • Honeymoon
  • Health
  • Cabins, Cottages, and Chalets
  • Holiday
  • Spa

Kemble Inn

Lenox, Massachusetts, United States
$200
1.800.353.4113

From its stunning 125-year old architecture to its array of modern amenities, Kemble Inn redefines luxury. Relax on their spacious veranda overlooking... more

Resort features:
  • Meetings
  • Holiday
  • Honeymoon
  • Luxury
  • Romantic
  • Wedding

Chambery Inn

Lee, Massachusetts, United States

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

Resort features:
  • Family
  • Golf
  • Fishing
  • Ski/Snowboard
  • Luxury

Wheatleigh

Stockbridge, Massachusetts, United States
$251
(1-413) 637-0610

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

Resort features:
  • Luxury

Hampton Terrace Bed and Breakfast Inn

Lenox, Massachusetts, United States
$175
800.203.0656

The Hampton Terrace Bed & Breakfast Inn is one of the elite Berkshire inns. Completely renovated and restored, this famous inn features stunning... more

Resort features:
  • Historical
  • Holiday
  • Luxury
  • Romantic
  • Bed & Breakfasts, Inns

Canyon Ranch in Lenox

Lenox, Massachusetts, United States
$1,130
855-460-1578

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

Resort features:
  • All-Inclusive
  • Meetings
  • Family
  • Health
  • Lake
  • Luxury
  • Nature
  • Pet Friendly
  • Spa

Black Swan Inn

Lee, Massachusetts, United States
$150
+1 (413) 243-2700

From double beds to king suites, Black Swan Inn offers luxury accommodations in the foothills of the Berkshire Mountains. Flat-screen televisions,... more

Resort features:
  • Family
  • Romantic
  • Ski/Snowboard
  • Luxury
  • Mountain
  • Lake
  • Honeymoon

Vacation Village at Berkshires

Hancock, Massachusetts, United States

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

Resort features:
  • Historical
  • Luxury
  • Timeshare

1896 House Luxury Inn

Williamstown, Massachusetts, United States
$179
1-413-458-1896

1896 House Luxury Inn is dedicated to creating an exceptional and unique lodging option in the Williamstown, Massachusetts area. With each suite... more

Resort features:
  • Golf
  • Historical
  • Luxury
  • Nature
  • Romantic

Showing 1-13 of 13 Luxury Resorts

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