Terzah recommends The Penderwicks by Jeanne Birdsall

One of the characters in this book, Jeffrey, wants to be a musician, but his mother wants him to go to military school. When some new friends, the Penderwick sisters, arrive for the summer, he finds he can be himself for the first time. The other books in this series are good, too.
Publisher description:
While vacationing with their widowed father in the Berkshire Mountains, four lovable sisters, ages four through twelve, share adventures with a local boy, much to the dismay of his snobbish mother.