A Separate Peace, by John Knowles -- This is one of those books that you read in junior high English class that you just can't shake. Gene and Finny are roommates at an exclusive northeast prep school during the early years of World War II. The plot centers around sarcastic Gene's jealousy of the friendly, athletic Finny, to disastrous consequences. But the school element is really important here. There's a sense of incredible urgency, knowing that the entire graduating class has just a few months left of childhood before they'll all likely be shipped off to war. Their school creates a protective, isolating bubble, their last days of invincibility, which ironically is exactly what forms the false sense of security that gets them into trouble. Dust off the copy that you never returned to your English teacher and read this one again.
I Am Charlotte Simmons, by Tom Wolfe -- Charlotte Simmons is the smartest person in her Appalachian mountain town. She's so smart, in fact, that she's accepted to an exclusive Ivy League college. The school setting in this novel creates the book's two main struggles: First, Charlotte's new experiences create a wall between herself and everyone she knew before college, including her own family. She can't relate to them anymore, and they can't relate to her. Second, Charlotte is no longer the big fish in a small pond, and when her identity as "the smart one" is challenged, it sends her reeling. I Am Charlotte Simmons is a study in how college changes and challenges us, and the growing pains that come with it.
Prep, by Curtis Steffenfeld -- Lee Fiora heads to the Ault School expecting to live out her high school years in a JCrew catalogue. Instead, she finds herself adrift among a set of ultra-privileged teenagers so jaded that they seem bored with breathing. Lee sits back and watches at first, trying to learn the intricacies of their world, but when she tries to join in, things get messy.
The Harry Potter Series, by J.K. Rowling -- This is going to skew the poll results something awful, but I would be remiss to write a post about school books without including the most famous of them all. Would Harry, Ron and Hermione's adventures be nearly as much fun if they went home to sleep in their own rooms every night? Who wants to read about Harry sneaking out of bed, slipping on the invisibility clock and walking up and down Privet Drive? There's so much going for these books, but the bedrock foundation is the school setting. No Hogwarts, no Harry.
A Little Princess -- Sara Crewe starts out as the richest student at Miss Minchen's Boarding School for Girls. She insists that she is a princess, but not in a bratty way. To Sara, being a princess means that she must be gracious and kind to everyone, even when she doesn't feel like it. When her wealthy father is apparently killed in India, Sara suffers a classic reversal of fortune and is forced to live in the attic and work as a servant girl. She is sustained by her powerful imagination, with which she refuses to see herself as anything less than a princess, no matter what indignities she must suffer.
Looking For Alaska, by John Green -- Culver Creek Boarding School stands out on this list. Although it's still a gathering place for trust-funded youths, scholarships abound, and for that reason the quirk-factor is high. Miles Halter joins his prank-loving roommate and one seriously foul-mouthed manic pixie dream girl in searching for a "Great Perhaps." The book is divided into "before it happened" and "after," and that alone should make you want to see what's going on here. But if you've ever wanted to read about a boarding school that didn't fit into the standard posh/privileged format, this one's for you.
I'm sure that I missed some good ones here, so please leave me suggestions for further reading in the comments!