I've always loved rereading book so in all honestly there's probably several books that fit this description for me. But I'm going to try to go with one book for each prompt and the book I'm sharing for this one is...
Are you surprised? I have a feeling this is probably a book that most people can claim they've read several times. I read it for the first time in 4th grade and it was one of the books (as well as the Little House books) that got me into historical fiction at an early age. I tried to read the whole series at that time, but my 8-year-old self couldn't, get past Anne of Ingleside in which Anne is a married mother and worried that Gilbert is having an affair. Understandable because reading about a marriage wasn't where my head was at that time.
Thankfully I decided to reread the whole series once I got to high school, and I'm glad I did, because while I love the first and original in the series I can't say it's my favorite. Instead I have to say my favorite is the last in the series, Rilla of Ingleside.
I do think it's a little amusing that this Anne of Green Gables book, that isn't even really about Anne, is my favorite. Sometimes I wonder who else stuck around and read the entire series to get to this one. And I'm definitely glad I decided to reread the books so I could read Rilla's story.
If it's been a while since you've read this book, and I think especially if you never got through the complete series, I think you should think about picking these up! And let me know, what book you've read more than 3 times. Maybe it's Anne for you too!