A hydraulic pressure cushioning device includes: a cylinder; a rod movably provided in the cylinder; a first piston valve section that is provided on the rod. The first piston valve section includes: a first piston member and a second piston member that form a channel; and a single first damping valve with which a first flow of the fluid from the first side to the second side in the channel and a second flow of the fluid from the second side to the first side in the channel are controlled; a bypass path which differs from the channel; and a free piston provided on the rod in such a manner that a flow of the fluid is switched between the channel and the bypass path in accordance with a movement position of the rod.

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