In this study, the damage characteristics of double-layer cylindrical shells with interlayer water subjected to small charge underwater contact explosion were investigated through experimental and numerical methods. At the same time, the distribution characteristics of the field pressure near the double-layer cylindrical shells and detailed bubble dynamics were revealed. The experimental results showed that there were crevasse and non-crevasse areas in the outer shell of the double-layer cylindrical shells, which form “inrushing bubbles” and “induced bubbles” in the interlayer water, respectively. Their subsequent bubble collapse behavior continued to impact the inner shell. Based on the traced analysis of the field pressure and deformation duration characteristics of the double-layer cylindrical shells, the load characteristics of the shock wave, interlayer bubble (inrushing bubble and induced bubble), and outboard bubble load sequence response to double-layer cylindrical shells were obtained.