In this study, the effects of zigzag hydrogen bonding and slidable cross-linking on the design of stretchable elastomers were explored. Poly(ether-thiourea) (TU), capable of generating strong zigzag hydrogen bonds without crystallization, was introduced as the main chain in the non-cross-linked region of the developed elastomer. Consequently, the toughness of the TU-based elastomer was 14 times higher than that of elastomers formed using linear poly(ethylene glycol), despite the relatively low molecular weight of TU (∼3k). When a slidable polyrotaxane cross-linker was introduced into the TU-based elastomer, its flexibility became twice as high as that of the rigid polymer cross-linker. Moreover, the mechanical properties of the elastomer were prevented from deterioration against repeated deformation under the limited strain condition of 150%.