A 1,3-diol bearing an 18-carbon alkyl chain was synthesized via the esterification of stearyl alcohol with 2,2-bis(hydroxymethyl)propionic acid. This 1,3-diol was employed as the chain extender to synthesize a linear multi-segmented polyurethane (PU) carrying long alkyl side chains. It was found that the linear PU was readily crosslinked with poly(β-cyclodextrin) [viz. P(β-CD)], i.e., the supramolecular networks were obtained. The supramolecular crosslinking was generated via the inclusion complexation of P(β-CD) with the long alkyl chains of PU. The more the incorporation of P(β-CD), the higher the crosslinking densities. Compared to the linear PU, the PU-CD networks had the enhanced Yong's moduli and tensile strengths. Thanks to the supramolecular crosslinking, the PU-CD networks had the shape memory properties. It was found that the recovery of shape was quite dependent on the quantity of the inclusion complexation linkages. In addition, the PU-CD networks can be reprocessed (or recycled); the reprocessed PU-CD networks had the recovery of mechanical properties as high as 95%. The dynamic exchange of inclusion complexation is responsible for the reprocessing properties. Furthermore, the reprocessing behavior was successfully utilized to reprogram the original shapes of the shape memory networks.