In the soft soil areas, such as Shanghai, artificial freezing method is adopted for constructing 98% underground engineering of metro side channel, pumping stations, and cross-river tunnels, but the method also causes notable problems of frost heaving and thaw collapsing on subway tunnel and surrounding geology environment. Although physical and mechanical properties of frozen soils have been studied, it is hardly sufficient for the research on the dynamic plastic deformation of freezing-thawing saturated silty sand. A remold-striping equipment was designed, and a method of saturating and freezing-thawing was proposed. The dynamic cumulated axial strain characteristics of freezing-thawing saturated Shanghai silty sand was studied using triaxial testing system. The experimental results reveal that compared with traditional compaction method, the remold-stripping equipment and proposed test methods provide an effect way for remolding, saturating, and freezing-thawing silty sand. The height and volume frost heaving ratio of intact saturated silty sand sample showed less influence with freezing temperature, but remolded silty sand frost heaving ratio increased as freezing temperature decreased. The axial permanent axial strain was closely related to the dynamic pore water pressure and less influenced by freezing temperature. Reducing vibration frequency resulted in smaller cumulated plastic strain. Increasing effect cell pressure and dynamic stress amplitude can significantly reduce the dynamic cumulated axial plastic strain of remolded freeing-thawing saturated sandy silt. Improved semi-logarithmic mode of cumulated permanent axial strain on freeing-thawing saturated silty sand was proposed and verified by experimental data, which could exactly forecast development trend of dynamic permanent axial strain.