Here's what rhymes with studdingsail.
fail sale sail veil hail shale vale inhale hale faille male scale mail pale tail tale avail jail nail rail entail frail gale whale bail stale wail assail bale dale pail snail flail kale unveil impale wale detail trail prevail email travail quail exhale quale bewail braille derail mainsail topsail grail wassail hightail curtail gunwale pigtail ponytail foresail monorail taffrail bobtail pellmell lugsail carrell fingernail countervail martingale hangnail tattletale nonpareil swallowtail