Middle English hol, hole, "a perforation, an opening, a pore;" from Old English hol (adj.) "hollow, concave;" as a noun, "hollow place; cave; orifice; perforation," from Proto-Germanic *hulan, which is reconstructed (Watkins) to be from PIE root *kel- (1) "to cover, conceal, save." Perhaps also partly from Scandinavian.
As an adjective, except in dialects it was displaced by hollow, which in Old English only was a noun meaning "excavated habitation of certain wild animals."
Germanic cognates include Old Saxon, Old Frisian, Old High German hol, Middle Dutch hool, Old Norse holr, Danish hul, hule, German hohl "hollow," Gothic us-hulon "to hollow out." For the English vowel change, see extensive note in OED (1989).
In reference to hollows or cavities of the body by c. 1300. As a small cavity into which the ball is to be sunk in certain games, by 1580s. As a contemptuous word for "small, dingy lodging or abode" hole is attested from 1610s; as the worst cell in a prison, by 1530s, originally of London's "Counter" prison for debtors and petty offenders.
The meaning "a fix, scrape, mess" is from 1760. In lower New England geography, "shallow cove, indentation of the coast" (1630s, as in Wood's Hole). Obscene slang use for "vulva" is implied from mid-14c.
The golfing hole-in-one is attested by 1914; as a verbal phrase (hole it in one) by 1913 (see hole (v.)). To need (something) like a hole in the head, applied to something useless or detrimental, is attested by 1944 in entertainment publications, probably a translation of a Yiddish expression such as ich darf es vi a loch in kop.