I remember finding this in my elementary school library and haven’t found it since. I remember that its a picture book about a man who I think is down on his luck and he hears about an offer to stay at a haunted castle for a night and win money or something. I think I remember that he was pretty like chill through the whole night? And had like bread and cheese, and a horse or mule? I absolutely loved this book and I’ve been thinking about it on and off for several years at this point and I miss it.
Esteban and the Ghost, maybe.
OH MY GOSH YES!!!! It’s Esteban and the Ghost!!! Thank you so much, I’m so excited to find this book again
This probably isn’t it, but The Ghost and the Sausage is about a poor boy who needs a place to stay for the night, but the only place he can find is a haunted house where a ghost comes down the chimney every night. The owners agree to let him stay there if he’s willing to try to get rid of the ghost. They give him a sausage for dinner, and when the ghost appears, the boy isn’t too impressed by him. The ghost deliberately annoys him to get the kid to knock him down, which is the key to breaking the curse that’s kept him haunting this house. When the elderly couple thank the boy, they ask him if there’s anything he wants, and all he wants is another sausage.
Is it the story about the dripping wet ghost that the man waiting for her freezes? If so, it was in the Arrow Book of Ghost Stories. I don’t remember the title of that particular story though!
A long shot, and some of those details aren’t familiar, but have you seen The Boy Who Wanted to Learn to Shudder, which has at least three pictures – drawn by Molly Bang? That is only one story in her collection, The Goblins Giggle (1973). Other stories in that book (three are Asian):
The old man’s wen.
Mary Culhane and the dead man.
A soccer game on Dung-Ting Lake.
The goblins giggle.