Build Two Pages of a Website

Hi! I am a college student and I am working on a website for a film fraternity. I already have everything bought (domain and all) and I have already done some work on WordPress in terms of design and functionality. I have five pages on my website's menu and I only need help in one. In basic terms: I need to establish a page called "Members" that will require a member log in (therefore, I will also need the ability of creating the different usernames and passwords as an administrator). If the log in is not successful, then an error message should appear, but if it is successful I want the user to be redirected to a sub page where the member can click on a link called "Equipment Reservations". "Equipment Reservations" is a sub-page as well in which the user will be able to make some reservations. Basically, I want it to be very user friendly (I have an example I can send), and I want it to be like a shopping cart, that also enables a calendar at check out so the user can choose the dates of the reservation. Thank you!