The COVID-19 pandemic has severely damaged the recreational travel industry due to uncertainty and restrictions imposed on travel and tourist destinations. Recent research has shown that COVID-19 has sped up the application of new technologies and contactless service innovations within tourism and hospitality operations. For example, implementing an automation interface through robotics or digital technology can simplify stay operations while complying with social distancing. Ideally, it can be one of the solutions to run safer, faster operations in the service process that will help recover the hotel business. Notably, “unmanned” devices and robots are commonly built to interact with customers and are adopted to provide contactless services. Therefore, this research was aimed at investigating how customers will be influenced by experiencing the contactless services at the luxury hotels, particularly during the check-in process, by using qualitative research methods including interviewing target customers of Generation X, building the Persona, and constructing a Customer Journey Map (CJM). This research shed light on the hospitality businesses and recreation industry that will provide a better understanding of the customer experience related to the self-check-in process and contactless digital services caused by COVID-19.