Booking calendar and search filter!

Hi wordpress forum! This is my first post.

I am doing just fine with most of my informational sites and those requiring just a few simple plugins which feels great but i’ve got a problem now.

I need to be able to create a website that allows for hotel booking. I used a custom post to create properties and now wanna use a booking plugin that can handle more than one property, and also have built in search functionality so that people can search based on availability through these properties.

I really don’t know where to start on this one. Any questions and advice will help!