In nanosized structures as the surface area to the bulk volume ratio increases the classical continuum mechanics approaches fails to investigate the mechanical behavior of such structures. In perforated nanobeam structures, more decrease in the bulk volume is obtained due to perforation process thus nonclassical continuum approaches should be employed for reliable investigation of the mechanical behavior these structures. This article introduces an analytical methodology to investigate the size dependent, surface energy, and perforation impacts on the nonclassical bending behavior of regularly squared cutout nanobeam structures for the first time. To do this, geometrical model for both bulk and surface characteristics is developed for regularly squared perforated nanobeams. Based on the proposed geometrical model, the nonclassical Gurtin-Murdoch surface elasticity model is adopted and modified to incorporate the surface energy effects in perforated nanobeams. To investigate the effect of shear deformation associated with cutout process, both Euler-Bernoulli and Timoshenko beams theories are developed. Mathematical model for perforated nanobeam structure including surface energy effects are derived in comprehensive procedure and nonclassical boundary conditions are presented. Closed forms for the nonclassical bending and rotational displacements are derived for both theories considering all classical and nonclassical kinematics and kinetics boundary conditions. Additionally, both uniformly distributed and concentrated loads are considered. The developed methodology is verified and compared with the available results and an excellent agreement is noticed. Both classical and nonclassical bending profiles for both thin and thick perforated nanobeams are investigated. Numerical results are obtained to illustrate effects of beam filling ratio, the number of hole rows through the cross section, surface material characteristics, beam slenderness ratio as well as the boundary and loading conditions on the non-classical bending behavior of perforated nanobeams in the presence of surface effects. It is found that, the surface residual stress has more significant effect on the bending deflection compared with the corresponding effect of the surface elasticity, Es. The obtained results are supportive for the design, analysis and manufacturing of perforated nanobeams.