We propose a $p$-multilevel preconditioner for Hybrid High-Order discretizations (HHO) of the Stokes equation, numerically assess its performance on two variants of the method, and compare with a classical Discontinuous Galerkin scheme. We specifically investigate how the combination of $p$-coarsening and static condensation influences the performance of the $V$-cycle iteration for HHO. Two different static condensation procedures are considered, resulting in global linear systems with a different number of unknowns and non-zero elements. An efficient implementation is proposed where coarse level operators are inherited using $L^2$-orthogonal projections defined over mesh faces and the restriction of the fine grid operators is performed recursively and matrix-free. The various resolution strategies are thoroughly validated on two-and three-dimensional problems.