Shelterbelts provide essential protection against wind erosion and soil degradation, as well as protection for fruit-bearing plants and crops from strong winds. Enhancing their sheltering capabilities requires optimizing their pattern and orientation, as well as defining their height and desired canopy shape, according to the desired performance. In this work, Large Eddy Simulation is employed to investigate the flow field and windbreak effectiveness of single and double-arranged shelterbelts characterized by different geometry and resistance to the air passage for neutral atmospheric condition. In particular, the canopy of the shelterbelts is modeled as an isotropic porous medium immersed in atmospheric boundary layer flow using the Darcy–Forchheimer model. Results show that a shelterbelt with a rectangular-shaped cross-section and a large canopy height results in the most significant reduction in mean wind speed and TKE, thus providing a large wind-protection region. As the spacing distance of double-arranged shelterbelts increases, the protection zones formed by both shelterbelts are reduced. The systematic comparisons of flow patterns, drag force coefficients, and windbreak effectiveness indicators of a series of single and double-arranged shelterbelts are essential for optimizing the design and management of shelterbelts.