Tourist interaction and interpretation of the heritage are placed in the context of heritage conservation, recognising the importance of the property and its current and future use [24]. Cultural significance, which encompasses aesthetic, historical, scientific, social and spiritual dimensions, is relevant to past, present and future generations and has implications for tourism [38]. In this context, the experience is improved with the contribution of contemporary technological developments, which allow recommendations to be enriched with meaning, identified with the context and aggregated value [4, 15, 48, 55]. Concepts related to the technologically mediated accommodation experience in classified properties will be highlighted, framed by aggregated information, intense connectivity and constant synchronisation, which tend to be efficient and meaningful. We intend to translate relevant implications at the management level—given the role of stakeholders, active participants in the co-creation of the experience, using their digital selves to access information infrastructures and add value, at the public policy level—given the importance of technological infrastructure, its implementation and regulation; as well as contributing to the existing literature on this important topic by highlighting key concepts and their interaction.