We analyze environmental determinants of roost site selection by tree gleaning passerines wintering in a Mediterranean montane oakwood at a craggy area of high variation in altitude and hill-shading pattern. We hypothesize that in temperate latitudes of cold winter climate, birds should spend the night in areas of low altitudes, higher temperatures, and higher solar radiation in order to minimize thermoregulation costs during resting time and to improve foraging conditions just before and after roosting. We study night occupation of woodland locations by the presence of feces in 159 wooden nest boxes (i.e., under identical controlled roosting situations). We employ GIS methods to quantify solar radiation at each location surrounding the nest boxes and data loggers to measure air temperature in the field. Birds prefer to roost in forest patches with higher solar radiation, where the period of light available for foraging is extended and thermoregulation costs during daytime are minimized. They also selected woodland patches with taller trees, a pattern consistent with their foraging preferences for trunks and branches. Other environmental variables played a negligible role in determining the selection of roost sites. Here, we show, for the first time, the importance of sun radiation determining where to spend the night in wintering birds and call attention on considering the thermal space in forest management. Forest management should preserve woodland patches with taller trees more exposed to solar radiation to enhance winter habitat suitability for birds in these Mediterranean oakwoods.