Winston married Maria Garrard Dudley (1836–1882), daughter of
General Ambrose William Dudley and Elizabeth Garrard ( Talbot) Dudley. Before his wife's death in 1882, they were the parents of six children, including: who married Grace Farwell, a daughter of
U.S. Senator Charles B. Farwell, in 1888; After his death, she married Robert Greaves McGann in 1906. • Bertram McIntosh Winston (1868–1933), who married Anne Odell (1869–1950), a daughter of J. W. Odell, in 1901. After his death, she married Victor Elting (1871–1956) in 1904. • Ralph Talbot Winston (1878–1948). In November 1896, he married Sallie Reeves Hews (b. 1872), a daughter of Edson Lawrence Hews, at Trinity Church in
New Orleans. In poor health, Winston retired to
Florida in his later years, dying near
Magnolia Springs, Alabama on February 19, 1904. He was buried at
Graceland Cemetery in Chicago. After his death, in 1906 his widow married the Rev.
ZeBarney Thorne Phillips, an
Episcopal clergyman who served as
Chaplain of the Senate from 1927 to 1942.
Descendants Through his eldest son, he was a grandfather of
Garrard B. Winston,
Under Secretary of the Treasury from 1923 to 1927. ==References==