Vinehall School was built in 1838 by Tilden Smith, a partner in Hastings Old Bank as his family home. However, he was declared bankrupt in June 1857 and just under a year later Vinehall was sold to Felix Champney for £20,170. His stay was brief, and in October 1860 Vinehall was sold again, this time to William Rushton Adamson for £35,700. For the next 42 years Vinehall remained in the Adamson family who renamed it Rushton Park. In 1902, the Ashton family bought Vinehall and enlarged the house to create the building we recognise today. It is believed that the great Joseph Paxton designed the grounds. On the death of Lady Ashton in 1938, the house was sold to the Jacoby family. At the time, Mary Jacoby was headmistress of nearby Battle Abbey School for Girls and she saw the opportunity to set up her son, John and his wife, Nell with a neighbouring boys’ school. Vinehall became a school in the late summer of 1938 with 6 pupils on roll.
During the Second World War, the School was evacuated to Killerton Park in Devon along with a local girls’ school. The School returned to its Robertsbridge home after the war and in 1946 was bought by Major Tom Stuart-Menteath. He and his wife ran the school until 1957 when his stepson, Richard Taylor and his wife Pat continued running the school. Many of the old traditions of the school began under their care, for example, the dormitories acquired their unusual names (Squirrels, and Hurricanes). The Taylors also had the foresight to build an indoor heated swimming pool, still in use today.
Richard and Pat Taylor handed the school over to their son-in-law David Chaplin in 1977. He and their daughter Sally remained until 2002. During their stewardship the school (which was already a charitable trust) took ownership of the whole estate and a major period of growth occurred. Pupil numbers rose throughout the years and many exciting developments followed, making Vinehall one of the best-equipped prep schools in the country. In the recent past, the purpose-built Pre-Prep was added as was a theatre, sports hall and in 2000,the magnificent Millennium Library and classroom complex. In 2002, the Chaplins handed over a thriving school to Mrs Julie Robinson was Head until until summer 2010 before Mr Richard Follett, who led the school until July 2017. Joff Powis is the current Headmaster.