I can’t think of any video game that fits that description. But I wish I got into RPGs earlier. My first role playing experience was near the end of my first year of uni. I wish I could have played D&D or other RPGs from when I was in high school. They’re such a blast.
I just want to point out that “the solstice marks the start of the season” is not a universal fact. Here in Aus, we mark the start of summer as 1 December, and so if I were to take my perspective and apply it to the northern hemisphere, I would say that for you, Christmas is about a third of the way through winter.
The difference here is technically referred to as “meteorological” vs “astronomical” seasons. I’ve always thought meteorological seasons make far more sense because they much better reflect reality. Winter is defined by cold weather and short days. The winter solstice is already very cold and it has the shortest day. It is absurd to put the shortest day at the very beginning of winter. If you wanted to have an astronomically-based calendar, the solstice should mark the very midpoint of winter, with the season starting precisely halfway between then and the autumnal equinox.
But also, as the other user mentioned, some places have entirely different season systems. Seasons are, fundamentally, a human creation. The notion that weather patterns change throughout the year is a universal fact, but what we call those changes and how many categories we separate it into is human. Many cultures have their own systems with more or different seasons. Many tropical areas have traditionally only observed “wet” (or monsoon) and “dry” seasons. In ancient Egypt, the flooding of the Nile marked an important seasonal change. And South Asia uses a variety of different 6-season systems, such as the Hindu, Bengali, and Tamil calendars.