having done some work for a few medium and high(ish)end hotels i can say they DO care - but ONLY IF it becomes public. No hotel wants to be publically known for being somewhere that men bring prostitutes back to. That would damage their reputation and business model.
However, if you and the lady are descreet, dress and behave appropriately they will not not know or turn a blind eye. Afterall they want your business too! So just be sensible, descreet and yes maybe meet her outside and walk in confidently and know where you are going (not having to look around and perhaps drawwing attention to yourself). It goes on a lot and only the daft ones have any problems!