The geometries of the –CH3 and –CH2OH modified β-cyclodextrin {i.e. (β- CD(R) m ( R = –CH3, –CH2OH ; m = 0, 1, …, 7)} and the energetical behaviors of one trans-Resveratrol (TR) molecule including inside their cavities were studied by using ONIOM (B3LYP/6-31G*:PM3) method. The most outstanding geometrical characteristic of the β- CD(R) m is that their inside radius (r) are varied with different chemical modifications. The released energies for one TR molecule passing through or rotating inside the cavities of β- CD(R) m are predicted to be related with the inclusion schemes (from narrow side or wide side of the cavity), the values of the inside radius r, and the types (– CH 3 or – CH 2 OH ) and number (m) of the substituted R groups. Our calculations also suggest that the formation of H-bonds in the inclusion interaction is the main factor to stabilize the formed inclusion complexes, i.e. the TR @β- CD(R) m( R = –CH3, –CH2OH ; m = 0, 1, …, 7).