Perhaps the most intriguing chapter in Woodhill Park's history involves its connection to the Kennedy family. Lord Harlech and President John F. Kennedy had known each other since the 1930s, and Lord Harlech became one of the president’s closest friends, often staying at the White House. The president told friends that next to McGeorge Bundy, Kennedy’s security adviser, Lord Harley was the most brilliant man he had ever met. He was leading advisor to Kennedy during the Cuban Missile Crisis of 1962.

This friendship with the Kennedy family continued after JFK's assassination, as evidenced by Jackie Kennedy and her brother-in-law, Bobby Kennedy, both staying at Woodhill Park. Lord Harlech's proposal to Jackie Kennedy years after the death of her husband is catalogued in many letters. These historical ties add a layer of international political and personal intrigue to Woodhill Park's history.