Accurate characterization of the resilient behavior of the base course materials under different climatic conditions is critical for the design of reliable and cost-effective pavement structures. In Alaska, the resilient behavior of base course materials usually undergoes significant variation due to seasonal change and extreme climatic conditions. Previous studies have revealed that the resilient behavior of base course materials could be significantly influenced by the freezing process. In this study, the freezing process under two extreme conditions (i.e., free and no water access conditions) that base course materials could possibly experience in the field was simulated using a one-dimensional frost heave cell. The influences of the water access condition during freezing on the frost heave and resilient modulus (MR) of the base course materials with different fines and initial water contents was assessed based on the results from the freezing process and repeated load triaxial tests. A pressure plate test was also performed to build the relationship between suction and water content of soils with different fines content. Suction was then introduced to model MR of the materials tested under unfrozen conditions before and after a freeze–thaw cycle. The adoption of suction significantly simplified the equation for MR prediction. Finally, structural analyses were conducted using BISAR and Alaska Flexible Pavement Design (AKFPD) software and the results revealed that free water access during freezing can significantly accelerate cracking and reduce pavement service life.