Owing to their dynamic natures, rotaxane-based polymers are attractive motifs for developing stimuli-responsive materials. However, the accurate control of the rotaxane structure, which can be achieved via multistep synthesis, is key to utilizing the material. Concurrently, implementing a scale-up synthesis procedure to exploit the application potential of rotaxane-based polymers induces structural ambiguities, thereby presenting a significant trade-off between realizing inexpensive production and defined structures. To overcome this rotaxane-synthesis challenge, cyclodextrin (CD) can be employed as a promising alternative owing to its low production cost. Thus, this study presents an overview of the precise synthesis of CD-based rotaxane and its application to polymers to simultaneously ensure inexpensive production and realize defined structures.