Born on 5 August 1857 at Littleton Pannell, West Lavington, Wilts, the son of Thomas Holloway, a WM local preacher. The family moved to London, where his older brother James established a successful building firm, joined by Henry and other members of the family. In 1882 Henry with his older brother Thomas (1853-1914) set up the family firm, Holloway Brothers, and in 1889, on the death of James, Henry took over the family business. Among their contracts were new naval barracks at Chatham, the Admiralty Building on Horse Guards Parade and the new General Post Office, and they later won important civil engineering contracts.
He was a leading figure in the new church on Balham High Road and became a fervent Methodist and temperance advocate . Under the influence of Hugh Price Hughes he was a supporter of the Forward Movement and in particular of the [Entry:2966 West London Mission]]. He was President of the London Branch of the Laymen's Missionary Movement and encouraged the early moves to establish a Methodist theological college in Cambridge.
Holloway Brothers were the main contractors, in collaboration with the architect W.W. Pocock, in the major refurbishment of Wesley's Chapel in 1891. On its completion Holloway Brothers presented two finely carved oak chairs for the baptistry and a lectern; one chair has a carved head of John Wesley with the quotation, 'The best of all is God is with us'. The other commemorates 'our dear brother James Holloway'.
Henry was sometime President of the Institute of Builders and of the Federation of Civil Engineering Contractors. He was knighted in 1917 for his contribution to the war effort in providing housing for munitions workers. He died on 5 August 1923.