Hello darling!
Being willing to procure accommodations is a sweet thing. You should be able to get a room anywhere you please, unless you plan on meeting with more than one lady in a day.
The trick to eliminating awkward inquiries is the woman you choose to spend time with. She should be dressed properly like a HDH (High Dollar Hottie), and not like a HHH (Harry Hines Ho). The hotel staff has no idea why you're there, and any woman that visits you should be able to pass for a colleague or a significant other. Either way, it's none of their business.
Have fun!