(1) Background: In the context of differences among countries developing pre-entrepreneurship ecosystems in relation to agritourism, the need to define the specific challenges and facilitators in the group of post-communist countries is recognised. Given that, we aim to examine the differences between the countries belonging to the former USSR and the satellite countries of the former USSR. (2) Methods: For the realisation of the intended objective, we analysed studies of the literature on the subject, in terms of the theoretical treatment of the entrepreneurial eco-system in the field of agritourism, and current legal acts. Our own observations from stays in the regions in question were also used, along with statistical methods concerning the density of the transport network, comparative analysis of historical and political conditions, and SWOT analysis. (3) Results: Substantial differences were found between the components of the agritourism entrepreneurship ecosystem in Poland and Kazakhstan, primarily related to the level of transport infrastructure density (satisfactory in West Pomeranian Voivodeship, insufficient in North Kazakhstan), tradition of individual farming (well established in Poland, poorly present in Kazakhstan), support for agritourism development by central and local authorities (relatively high in Poland, incidental and with a short history in Kazakhstan), and finally, differences in the target group of agritourism service recipients (stable in Poland, undefined in Kazakhstan). (4) Conclusions: The research leads to the conclusion of the heterogeneity of the determinants of the development of the agritourism entrepreneurship ecosystem in countries collectively defined as post-communist. There are clearly different challenges and facilitations resulting not so much from the past political system as from the ethnic-historical considerations, the position of agriculture in the economy, and the degree and effectiveness of the involvement of administrative authorities in the development of agritourism. The study leads to a recommendation on the need for more efficient targeting of agritourism consumers abroad.