Based on historic scripts and modern literature, an analysis, comparison and description has been conducted on the concepts of motels and caravanserais. The goal of the analysis is to determine the similarities and distinctions between the historical wayfarer stops and inns of the Middle East and Southeast Europe and the modern guesthouses. They were compared based on their functions, looks, locations, history and architecture as well as how they advanced through the history starting from their earliest appearances. A detailed analysis has been conducted on the architecture, content, development and role of caravanserais through various historic periods under the rule of the most notable dynasties in the various regions of the Middle East. The development of motels has been analyzed from the first appearances of free camps and cabins at the start of the 20th century up to their peak and their most notable examples that contributed most to their rise. Along with motels and caravanserais, the characteristics of khans are also analyzed as their characteristics are often mistaken with the ones of caravanserais.