Consumer behavior has changed dramatically over the years, and various economic, and, more recently, health crises have prompted a large number of industries, particularly the upscale hotel industry, to reinvent themselves. Adaptations are therefore necessary within the three temporal phases identified in the literature (expected, lived, and remembered experiences). This research explores how digital technologies have helped evolve the personalization of luxury customer experiences in upscale hotels (i.e., 4- and 5-star). We conducted a qualitative study of 22 upscale hotel professionals. The results show that digital devices influence the personalization of luxury customer experiences—in terms of both their dimensions and the phases of the customer journey—and the behavioral reactions of consumers. From a managerial point of view, these results allow all professionals in the upscale hotel industry to identify and activate the appropriate digital levers to offer personalized luxury customer experiences which are more in line with consumers’ new expectations.