Can I re-charge a card after a guest wins a chargeback?

Re-presenting a transaction that has already been charged back is one of the few genuinely dangerous shortcuts in this area. Card network rules treat a second submission of a disputed transaction outside the formal representment channel as a violation, and your acquirer enforces those rules through your merchant agreement rather than through a court. Consequences escalate from per-item fines to placement in a chargeback monitoring program to termination of your ability to accept cards at all. For a motel, losing card acceptance is an existential problem far larger than any single unpaid folio.

There is a legitimate version of what you are trying to do, and it runs through the same acquirer relationship. Representment is the mechanism for saying the reversal was wrong, and it exists precisely so merchants do not have to self-help. Use it, accept the answer, and then treat the shortfall as a debt like any other. The reason court is the clean route is not that it is faster, because it is not. It is that a judgment is enforceable against the person, cannot be reversed by their bank, and carries no risk to your payment processing.