well some short animes which i think are well made are :
- Zero no Tsukaima (2 seasons,1st has 13 episodes 2nd has 12 episodes)
basically where at a academy for nobles in an alternate dimension (All nobles have magic) they must summon a familiar and the main girl who is not so good at magic accidentally summons a japanese boy her age from our world to be her familiar. I can't really say much more without spoiling the series
- They are my noble masters (13 episodes)
The main guy and his sister run from their alcholic violent father and incidentally while looking for work they end up (After helping out a girl) being butler and maid for a famous woman. To put it simply its a harem anime and quiet funny/enjoyable with lots of references to other series.
- Air (13 episodes)
This ones very difficult one to explain since its very complicated (involving reincarnation and stuff). This animes a very depressing/sad one (especially episode 12). Episode 13 is basically a retelling of the whole series in one episode so up to you if u want to watch that one. But it fits the abstract anime you asked for.
Though to do the description they give officially is its about a boy who travels to a village to find a girl with wings his mother talked about (who could fly in the sky), while staying at a village to make some money he meets a girl while continually looking for the girl with wings. Well worth a watch for sure.
while both descriptions seem to not relate, they fit together well in the series