The synthesis of the nematic crosslinking agent (4′‐allyloxy‐benzoyl)‐(4″‐undec‐10‐en‐1‐oyl‐benzoyl)‐p‐benzenediolate ( M ‐ 1 ), the cholesteric monomer cholesteryl undec‐10‐en‐1‐oate ( M ‐ 2 ) and side‐chain cholesteric liquid crystalline elastomers is described. The chemical structures of the obtained monomers and elastomers were confirmed by FTIR and 1H NMR spectroscopy. Their mesomorphic properties and phase behavior were investigated by differential scanning calorimetry, polarizing optical microscopy, and X‐ray diffraction measurements. The influence of the crosslinking M ‐ 1 units on phase behavior of different elastomers prepared by a one‐step hydrosilation reaction was discussed. The elastomers containing less than 20 mol‐% of the crosslinking M ‐ 1 units showed elasticity, reversible phase transition and cholesteric texture. The experimental results demonstrated that the glass transition temperatures and isotropization temperatures of P ‐ 2 ~ P ‐ 6 increased with increasing the concentration of crosslinking M ‐ 1 units.