I've been moving in this direction a long time--probably since 6th grade (I've mentioned to people that I've been a Benedictine all my life and didn't know it until 2006). I've read a lot of books along the way, not all written by Benedictines but all sort of converging on this point. I became an oblate in October 2007 at Clyde Monastery. I started reading during the summer of 2006. And here are the highlights.
Bake and Be Blessed by Fr. Dominic Garramone. It doesn't sound like much, and it isn't much--a short book, each chapter about a different stage of bread baking and how we take that step and create an analogy for our spiritual lives. I read this in the summer of '06 during the 3 day long black out after the "Storm of the Century." I stayed up late, read it by flashlight, and was hunting down monasteries as soon as the lights came back on.
Wisdom Distilled From the Daily: Living the Rule of St. Benedict Today by Joan Chittister. This book takes different aspects of the Rule and of Benedictine life (hospitality, work, humility, stability, etc) and teases them out for what they mean for us in modern life, in places that aren't monasteries, for people who aren't monks.
The Rule of Benedict by Joan Chittister (well, the Rule isn't by her, it's obviously by Benedict, but this is a commentary). A wonderful translation and each daily reading has reflections from other traditions--mostly Eastern influences--that help draw out the truth of the Rule.
Becoming Fully Human by Joan Chittister. Each chapter of this book is a question, for instance, How is caring for the earth spiritual? Or When is war unjust? Each chapter is short and full of little vignettes.
How To Be A Monastic And Not Leave Your Day Job by Benet Tvedten. What it sounds like. A guide book for oblate candidates. It's dedicated, by the way, to my oblate director, who read and commented on it for him.
In Search of Belief, by (again) Joan Chittister. This is the Apostle's Creed, taken line by line. It troubled, shocked, heartened, and enlivened me when I read it the first time.
The Cloister Walk by Kathleen Norris. Many oblates start the tale of their journey with "A friend let me borrow the Cloister Walk..." Not true for me, but Kathleen's journey matches many folks' attempts to find a place in their system of belief.
Radical Hospitality by Daniel Homan and Lottie Pratt. The only thing wrong with this is that, written by two people with two very different styles/voices, it is jarring. And they refer to themselves in 3rd person, interspersing both writers in a single chapter. Sometimes I have a hard time getting past that. But the idea is solid and useful reminder.
Benedict's Way by Daniel Homan and Lottie Pratt. Daniel Homan, again, is a Benedictine priest, and Lottie is a friend of his monastery--I don't think she's an oblate. This is probably the most "popular spirituality" of all the books I own about Benedictine thought and spirituality. It is a jumping off point.
Praying the Bible: An Introduction to Lectio Divina by Mariano Magrassi is just what it says it is. Much more scholarly work, less accessible to the general public. But exactly what it claims to be.
The Quotidian Mysteries by Kathleen Norris. Quotidian means everyday. Mundane things. The dullness of life--laundry, dishes, carpools, that sort of stuff. This book is her attempt to find God there. I liked this one much more than the whole of the Cloister Walk, although bits of that one are gold.
Blessings of the Daily by Br. Victor-Antoine D'Avila-LaTourette (yes, that's his name...). This is one of those reflection-a-day books, but about a monastery in New England. I got this book because I also have his Year of Monastery Salads, which, oh my goodness, is so worth it.
There are others--a number of oblates besides Kathleen Norris have written books, although several of them kind of run together in my mind. There is a book by an oblate that discusses at length the Benedictine ladder of humility (flippantly put, the 12 step program for monks), which interests me, but honestly, her writing style isn't as good as mine. This grates on my nerves on many levels. So I don't read her stuff anymore...and this summer I am going to do my best to read Cistercian Michael Casey's The Undivided Heart. But I don't have it here because, well, I haven't read it yet!
The one non-Benedictine I'd put on this list is Thomas R. Kelly. He was a Quaker and wrote deeply about spiritual matters. A Testament of Devotion is the one I've read (he has a very short bibliography, dying young and published only posthumously).