Thermal behavior analyses on historical buildings provide design data, which can be utilized for the decision-making processes on their adaptive reuse and on constructional interventions as well as on the energy infrastructure planning for the historical settlements. With these analyses, as the energy consumption of historical buildings can be stated, it is possible to design thermal retrofitting measures in order to improve their thermal comfort status for ensuring their functional continuity. On the other hand, with the help of these works, the effects of parameters such as temperature and humidity on construction materials can be specified. Additionally, the information on the original thermal behavior of historical buildings can establish a significant data source on the subject of sustainable modern building design. The most common method for determining the thermal behavior of buildings is the use of building performance softwares. These softwares enable the 3D modeling of buildings with their physical (geometry, construction materials, etc.) and social (user profile, utilization intensity, etc.) attributes and consequently their analyses through thermal simulations. For these simulations, building performance software use local weather data. These data can be generated with specific climate software. However, upgrading of these software-generated data in compliance to the on-site weather readings will have the capability to enhance the reliability of building models as well as having the potential to be able to evaluate the different specific microclimate conditions throughout the settlements.  The aim of this project is to state and emphasize the significance of utilizing on-site weather readings within the processes of generating simulation weather data for the analyses of thermal behavior of historical buildings. In the scope of the work, outside air temperature and relative humidity values were read on-site at urban and rural traditional houses of the same historical settlement and the specified differences were evaluated. With this comparative evaluation, it was pointed out that the collected microclimate data demonstrate significant variations in different sub-settlements of distinct locations and topographical features within the same city.