Based on the concept of teleworkability, its sluggish determinants of industry structure and workplace culture, and the change in people’s valuation of rural amenities that happened during the pandemic, this paper analyzes their possible influence on counterurbanization during the pandemic in Sweden and Slovenia. We found signs of open (migration) as well as “hidden” counterurbanization (unregistered rural living) in both countries, stronger in Sweden than in Slovenia, and we found indications that industrial structure and national workplace cultures contributed to differences in the strength of the counterurbanization. In both countries, we found indications that the pandemic contributed to a shift in people’s relative valuation of rural vs. urban amenities. Thus, while the sluggish factors contributed to differences in teleworkability between Sweden and Slovenia, the chock implied similar reactions in the shift of the valuation of amenities. Ever since the counterurbanization of the 1970s, studies of the phenomenon have almost solely been completed within countries, and the few international comparisons that have been completed have been based on comparing the results of the national studies. This study is one of the very first ones that compares counterurbanization and its driving forces in two countries within the same analytical framework.