This study examines occupants’ perceptions of comfort, control, and adaptation in Colonial Revival style residences in the “Building America Climate” cold region of the United States. The research considered these buildings due to their attractiveness and availability in the study area. The research intends to address the following question—Do occupants’ perceptions of comfort significantly impact their perceptions of control and adaptation within the buildings? This study utilized indoor monitoring of variables in the summer, thermal comfort surveys (110 respondents), walk-throughs, observations, and informal interviews to collect data for analysis. The residents that perceived higher air movement and humidity also use control more often and are more often satisfied with the level of control. The differences between the mean neutral temperatures were within the range of 2.2 °C. On a seven-point scale, the mean thermal sensation votes (TSV) and thermal comfort (TC) were 3.25 and 5.05, respectively. The study revealed higher perceptions of the thermal environment among residents who spent longer hours in the buildings than those that spent fewer hours within the residences. The research implies that while there are limited options for control, the residents who spent longer hours in the buildings perceived themselves to be more comfortable and to be able to adapt better using available adaptive measures than those who spent fewer hours in the residences. The study notes that, as people migrate from one thermal environment to another, their adaptation level may change depending on certain factors, including the adaptive measures available to them. The research recommends the integration of transitional smart devices (such as remotely controlled thermostats, etc.), including control for the residents who spent fewer hours in those buildings.