Polydimethylsiloxane (PDMS) is one of the preferred materials for researchers to design smart flexible sensors or devices due to its excellent chain flexibility as well as the unique features of transparency, nontoxicity, and biocompatibility. To fulfill the requirement of the service safety and long‐term application, the development of healable PDMS‐based substrates is booming. However, it is still a big challenge to develop PDMS elastomers with good healing performance, high strength, high stretchability, and high toughness simultaneously. Herein, a healable, recyclable, and highly stretchable PDMS‐based elastomer is prepared by incorporating different supramolecular interactions including π–π stacking and hydrogen bonding into the matrix. This elastomer is fabricated via a one‐pot polycondensation reaction among bis(3‐aminopropyl)‐terminated PDMS , functional monomer pyrene diol and 1,6‐diisocyanatohexane. The mechanical properties and self‐healing properties can be easily tuned by varying the density of π–π stacking to hydrogen bonding. The resultant elastomer exhibits very high strength and high stretchability with a fracture strength of 7.46 MPa and fracture strain of 2174%, and it achieves nearly complete self‐healing (96%) at 110 °C for 1 h.