To explore the damage evolution law of cement-stabilized weathered sand under the action of freeze–thaw cycles, relevant experimental research was carried out on stabilized weathered sand with a cement content of 3%, including unconfined compressive strength (UCS), scanning electron microscope (SEM), and mercury intrusion porosimetry (MIP) testing. Using the surface appearance, mass, and UCS of the specimen, combined with the changes of microscopic characteristics, the freeze–thaw damage law and microscopic degradation mechanism of cement-stabilized weathered sand were analyzed. The test results showed that with the increase of the number of freeze–thaw cycles, the surface appearance of the specimen continued to deteriorate, the unconfined compressive strength gradually decreased, and the mass of the specimen first increased and then decreased. After nine freeze–thaw cycles, the specimen was seriously damaged, and the strength loss was as high as 55%. From a microscopic point of view, the freeze–thaw cycles caused the pore water inside the specimen to continuously change between ice crystals and liquid. Frost heave and shrinkage weakened the cement bond between the weathered sand particles and made the pores in the specimen develop and expand continuously. With the decrease of the number of micropores and the increase of the number of medium and large pores, the particle skeleton changed from a dense structure to a porous structure, which eventually led to the deterioration of the macroscopic properties of the cement-stabilized weathered sand.