Rural courtyard dwellings in cold regions are commonly characterized by low winter indoor temperatures, intermittent heating, solar heat gain, pronounced thermal fluctuations, and strong occupant adaptation. This study aimed to compare short-term winter indoor thermal conditions among three rural courtyard dwelling cases in Qingcheng Ancient Town, Gansu Province, Northwest China, and to examine the associations between operative temperature and multidimensional subjective thermal responses under the monitored conditions. Synchronized indoor–outdoor environmental measurements and 216 paired questionnaire records were collected during two winter survey days. To account for shared environmental exposure, the questionnaire records were organized into 66 dwelling–time clusters. The results showed that: (1) outdoor air temperature ranged from −13.34 °C to 13.24 °C, with a mean of −3.91 °C, while the mean operative temperature during the questionnaire periods was 11.31 °C and the mean thermal sensation vote (TSV) was −0.97, indicating an overall sensation close to slightly cool; (2) the dwelling with an added sunspace had the highest mean operative temperature, the ordinary brick–concrete dwelling exhibited the greatest temperature fluctuation, and the earth–wood dwelling remained cooler but relatively stable; (3) each 1 °C increase in operative temperature was associated with 75% higher odds of reporting a warmer TSV category (OR = 1.75, 95% CI: 1.53–2.00), while the two-way fixed-effects model estimated a 0.176-unit increase in mean TSV; and (4) higher operative temperature was associated with greater broad and clear thermal acceptability and a lower likelihood of preferring warmer conditions, with the study-specific neutral operative temperature estimated at 16.75 °C and a block-bootstrap 95% confidence interval of 15.66–18.40 °C. These findings provide field-based evidence of the associations between operative temperature and multidimensional winter thermal responses and offer an empirical basis for climate-responsive and heritage-sensitive thermal improvement strategies for rural courtyard dwellings.