Compatibility of plugin with intended use

I want to know if this plugin will allow me to set it up for the following functionality:
I have a vacation rental property with 2 homes.
During the prime summer months I rent by the week Saturday to Saturday and require that both homes be reserved.
During the Fall, Winter and Spring seasons I allow people to reserve a 2 night minimum and offer them the choice of 1 or both homes.
Can the plugin be set up to prevent people from reserving one home for a Summer season weekend?
I currently use a google calendar plugin and manually block out dates after they are reserved.