Dynamic and adaptive materials are powerful constructs in macromolecular and polymer chemistry with a wide array of applications in drug delivery, bioactive systems, and self‐healing materials. Very often, dynamic materials are based on carefully tailored cyclodextrin host–guest interactions. The precise incorporation of these host and guest moieties into macromolecular building blocks allows the formation of complex macromolecular structures with predefined functions. Thus, dynamic materials with extraordinary adaptive property profiles—responsive to thermal, chemical, and photonic fields—become accessible. This Review explores the hierarchical formation of dynamic materials and complex macromolecular structures from the molecular via the macromolecular to the colloidal and macroscopic level, with a specific emphasis on the functionality and responsiveness of the assemblies, specifically in biological contexts. A host of opportunities: Dynamic and adaptive materials play an important role in the chemistry of contemporary soft materials with applications in stimuli‐responsive, bioactive, delivery, and self‐healing systems. This Review highlights dynamic materials based on cyclodextrin host–guest chemistry and macromolecular building blocks.