This study examines the role of Heritage Hotels in shaping the identity of Greek tourist destinations. The research was carried out in two phases: first, the structural characteristics and spatial distribution of all Heritage Hotels across Greece were analysed. Then, the focus shifted to three regions with a high concentration of Heritage Hotels: Magnesia, Ioannina and Santorini (Thira), representing destinations with distinct geographical, developmental and tourism profiles. To explore how Heritage Hotels promote their historical and cultural identity through their digital presence, a detailed analysis of the websites of all Heritage Hotels in these regions was undertaken. The main findings show that Heritage Hotels meet several objectives of sustainable tourism development and are instrumental in preserving and enhancing local architectural heritage. This confirms that Heritage Hotels can play an important role in promoting and sustaining an authentic local identity. However, the study also indicates that the emphasis on historical narratives and cultural identity of buildings varies depending on the orientation of the destination. Furthermore, it highlights the importance of the hotels’ digital presence, particularly in preserving and promoting the authenticity of historical narratives, which is a critical factor in the overall attractiveness of destinations.