The courtyard is an ancient outdoor design space surrounded by walls or buildings, acting as a microclimate modifier in hot-dry climates. This is related to its geometry, such as high proportions of height-to-width (H/W) and north-south (NS) orientation by providing shade and decreasing heat stress on hot summer days. However, its effect during winter still needs to be discussed, especially in hot summer and cold winter conditions (such as in semi-arid climates). This research studies the winter thermal comfort of a typical courtyard geometry suitable for hot summer conditions in a semi-arid climate. A literature review supports the identification of typical courtyard geometry addressed for hot summer conditions. Then, field measurements of the external surface temperature of courtyard interior orientations, microclimatic variables, and the Predicted Mean Votes (PMV) of occupants inside the courtyard were performed. The results indicate high correlations between PMV and courtyard interior orientations with the H/W ratio regarding cold stress. Thus, north-east and South-East orientations and H/W ratio less than (< 0.8) are recommended for better winter environmental conditions in semi-arid climates.