All you have to do is to be meticulous in your start and end dates for each category. In other words, the dates covering the four seasons you mention had better cover 365 (or 366) days exactly for each type of room, each amount of occupants, etc.: no overlaps; no gaps.
If you cover all these bases correctly, all you have to do in a query, or in VBA, is use the >, <, =, >=, and/or <= mathematical symbols on the various dates to find the total invoice amount.
Good luck. It really is tedious, but very rewarding when it works like a charm.
SL