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Autonomous recovery for original states is a distinctive property in living organisms that stimulates the development of artificial materials with unprecedented responsiveness and autonomy because such bioinspired functions can be potentially applied to biomedical materials and devices. Therefore, excellent responsivity to external subtle stimuli is highly desirable. We designed a poly­(NIPAM-co-CD-co-DBD) bearing a β-cyclodextrin (CD) host and dimethylaminosulfonyl-2,1,3-benzoxadiazole (DBD) guest to realize highly responsive temperature-induced autonomous reswelling due to interchain cross-linking of the polymer chains via CD–DBD complexation, though a previous poly­(NIPAM-co-CD) needs stronger temperature stimuli for its autonomous reswelling. Density functional theory calculations indicate a promising steric conformation of the CD–DBD complex for the autonomous reswelling. Thus, a small temperature change, heating with 0.5 °C steps, can lead to repeated autonomous reswelling. Furthermore, the autonomous reswelling was successfully detected based on the fluorescent character of DBD, which proved the capability for visual detection of the autonomous reswelling.