Bolton was "a dapper ladies' man, who, having divorced his first wife, became ensnared in a succession of entanglements with chorus girls and singers." He was married four times. With his first wife, Julia, "née" Currey, whom he married in 1908, he had one son, Richard M. Bolton (1909–1965) and one daughter, Katherine Louisa "Joan" Bolton (1911–1967). With his second wife, opera singer Marguerite Namara, to whom he was married from 1917 to 1926, he had a daughter, Marguerite Pamela "Peggy" Bolton (1916–2003), who was his only child to outlive him. His third wife was a chorus girl, Marion Redford, whom he married in 1926. Redford had already given birth to Bolton's son, Guy Bolton Jr., known as "Guybo" (1925–1961) before his divorce from Namara. Bolton and Redford divorced in 1932. There were no children of his fourth marriage, to the playwright Virginia de Lanty. This marriage lasted from 1939 until her death in 1979.