Old Money Resorts: Where American Royalty Stay and Play

There's a reason The Breakers' reputation precedes it. This 140-acre resort, first built in 1896 (and reconstructed in 1926), resembles a Renaissance palace, and it's seen more than its fair share of American royalty over the years; Andrew Carnegie, J.P. Morgan, William Randolph Hearst, and various Astors, Rockefellers, and Vanderbilts have all walked the halls at this posh spot. No other hotel in Palm Beach can come close to matching the luxury found at this iconic property.

This New York hotel is synonymous with luxury, and has carved out a prominent place in 20th-century culture. Truman Capote threw his famous Black and White Ball here; in North by Northwest, Cary Grant was captured by spies in the hotel's famous Oak Bar; and F. Scott Fitzgerald staged part of The Great Gatsby here. When The Plaza first opened its residences, Mr. and Mrs. Alfred Gwynne Vanderbilt were the first to sign up.

The Cape has long been a cherished spot for the American rich to summer, and the Chatham Bars Inn has been drawing America's wealthy and powerful since it opened in 1914: Past guests include Henry Ford, Henry Morganthau, and William Rockefeller. The true Cape-Cod style architecture is complemented by lovely interiors -- upholstered wingback chairs, antique-style turned-leg furnishings, and seafaring decor.

Opened in 1926, the Biltmore is a timeless luxury hotel and a registered historical landmark. Before the stock market crashed in 1929, guests included the Duke and Duchess of Windsor and several Vanderbilts. The 150-acre property includes a 315-foot copy of the Giralda bell tower in Seville, Spain, and the largest swimming pool in the continental United States.

The North Shore of Long Island was once home to the estates of many of America's aristocratic families -- the Vanderbilts, Whitneys, Roosevelts, and Morgans, among many more -- earning it the nickname the "Gold Coast." Oheka Castle was the largest of these estates, and the second largest private residence in the entire country. Financier Otto Hermann Kahn hosted numerous parties at the estate during the 1920s (the Gatsby era) that were attended by royals and Hollywood celebrities. Today, Oheka Castle is a hotel with 32 rooms, and is used as an event space for high-profile weddings and galas.

Built in 1909 by Alfred Gwynee Vanderbilt, the Vanderbilt Grace Hotel is an original Newport mansion. Today, it's an elegant luxury hotel that retains the original architecture; the handsome brick building, the grand double staircase, and details such as wainscotting and crown molding add to the historic charm.

Los Angeles may smack of celebrities and new money, but Old Hollywood -- when the likes of Cary Grant, Fred Astaire, Ingrid Berman, and Marilyn Monroe graced the silver screen -- is another thing entirely. Dating back to 1912, the Beverly Hills Hotel is one of the grand dames of Tinseltown; almost every iconic actor of the Hollywood Golden Age passed through the "pink palace's" hallowed halls. Today, the dignified hotel still sees its fair share of VIPs.

Originally built in 1925 by William Vanderbilt II as a winter estate, Fisher Island is a private island, residential community with a 45-room hotel. Peacocks freely roam the lush grounds, and the original Vanderbilt Mansion now houses two of the island's restaurants, where tuxedo-clad waiters see to guests' every wish.

A century ago, Thomas Henry Chirgwin built a luxury hotel and called it The Colonial Inn. The inn had all the modern amenities guests at the time might have wanted -- such as electricity and indoor plumbing. Since its opening, the inn has counted a number of celebrities among its guests, including Howard Hughes, John F. Kennedy Jr., and Jacqueline Kennedy. Today, the inn is known as the Vineyard Square Hotel and Suites, a modern luxury property on quaint Martha's Vineyard, which remains a popular summer playground for East Coast notables.


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