My number one choice would definitely be Let it Snow by John Green, Mureen Johnson, and Luren Myracle. This book contains three different holiday romances that all occur in the same town. All of the stories connect in the cutest ways. This book is the EPITOME of a cute, feel-good winter read.
When I think of winter reads, I think of books that make you feel as good as a warm fire does. Dash & Lily's Book of Dares by Rachel Cohn & David Levithan does that. The first time I finished this book I couldn't help but smile. And doesn't that cover just scream winter?
If you are more of a paranormal book person I would recommend Shiver by Maggie Stiefvater. This book has just what you need: a wintertime setting, a cute small-town, a simple but complicated love, and werewolves!
What is your ideal wintertime read?