This book constitutes the refereed proceedings of the 5th Conference on Digital Encounters with Cultural Heritage, DECH 2017, and the First Workshop on Research and Education in Urban History in the Age of Digital Libraries, UHDL 2017, held in Dresden, Germany, in March 2017. The 11 revised full papers from DECH 2017 and two revised full papers from UHDL 2017 presented in this volume were carefully reviewed and selected from 33 joint submissions. The papers are organized in topical sections on research on architectural and urban cultural heritage; technical access; systematization; education in urban history; organizational perspectives.