The purpose of this study is to investigate the diffusion of smartness in hospitality and, furthermore, the assimilation of smart technologies in hotel business units. A qualitative exploratory investigation with an abductive research approach was adopted and data were collected through in-depth interviewing of 39 hotel managers in the highly advanced hospitality industry in the United Arab Emirates (UAE). Analysis of the data was conducted inductively to elicit themes within the technological, organizational, and environmental contexts and to mark trailheads for future research. The study yielded important insights into how barriers to the diffusion of smartness can be surpassed, and how smart technologies can be assimilated into existing hotel organizational structures and operations. The proposed aggregate dimensions for achieving assimilation of smart technologies in hotels highlight the importance of organizational sustained learning and smart networks synergism while shaping configurational system innovations.