Henry Holloway Plantation Ledger, 1796-1810, records the business activities of the Holloway family's plantation and the personal financial activities of Henry Holloway. The ledger records the accounts of individuals, estates, and businesses that Holloway managed or with whom he conducted business. Each account lists transactions in chronological order, and each transaction includes the date, the type of transactions, and monies debited and credited.

The accounts connected with the plantation document purchases made for items such as trees, oxen, horses, sugar, and coffee. Several accounts include a listing for the hiring of slaves; although, no detail is provided as to what type of work they performed on the plantation. There are also entries for the plantation overseer that concern his wages and providing him his share of wheat and corn. Holloway also kept records of the quantities of wheat seeded, used by the family, and sold.

The personal financial accounts of Henry Holloway document the individuals and businesses with which Holloway conducted business. Many of the accounts detail Holloway's family expenses and document tuition paid and purchases of clothing and books. There are several account entries that detail the settlement of the estate of Robert Holloway who died around 1802. Holloway also helped to support his sister Betsey Yancey, wife of Robert Yancey. Her account entry includes the following note written by Holloway: "It is impossible for the Writer to say how unhappy he has been made from the imprudence of Capt. Robert Yancey. He has brought a wife & children to want from his drinking as well as gambling. The above articles is given to a sister who is in want of much more, and I wish I had it in my power to give it."