A series of polyurethane elastomers (PUEs) were synthesized from an aromatic diisocyanate (4, 4'-diphenylmethane diisocyanate); a polyether polyol (polytetramethylene glycol, molecular weight: 1000), polyester polyol (polycaprolactonediol, molecular weight: 1000, or polycarbonate diol, molecular weight: 1000); and β-cyclodextrin (β-CD) as a cross-linker. The effect of the polyol on the morphologies and chemical, thermal, and mechanical properties of the resultant β-CD-based PUEs were investigated in this study. The obtained films were characterized via solubility and swelling tests (chemical properties), differential scanning calorimetry (crystallinity degree), dynamic mechanical analysis (thermal stability), thermogravimetric analysis (thermal stability), tensile testing (mechanical properties), nuclear magnetic resonance spectroscopy, infrared spectroscopy, atomic force microscopy (morphology), contact angle determination (morphology), and scanning electron microscopy (morphology).