This study discusses the historical evolution of inns and innkeeping in Jewish society in Roman Palestine and examines their social implications, and in particular, the relationship between opposite ends of the social ladder, and what this meant for the status of women. After a sketch of innkeeping in the Ancient Near East from the third millennium B.C.E., the focus is on the Roman period. During that period, it is argued, innkeeping, originally associated with sexual promiscuity and the lowest strata of society, gained acceptance only with difficulty in the religiously conservative Jewish society of the time. Nevertheless, in time it became quite common and rabbinic sources of the 2nd and 3rd centuries C.E. take it for granted.