The books described below are my favorite books on Buddhism and/or mindfulness meditation. I have tried to describe what I like (and in some cases, don't like) about each one. I wholeheartedly recommend all of them!
What to read first?
If you are a beginner looking for mindfulness instructions and some reasons to practice, pick up Radical Acceptance or The Mindful Geek or both, depending on your inclination.
If you want to learn more about Buddhism and gain a broad perspective on the path, pick up A Path With Heart.
If you've been meditating for a while and want to increase your wisdom and freedom, pick up Dancing With Life.
If you want to "get better at" meditating [warning: attachment to the "quality" of your meditation can be a trap], pick up The Mind Illuminated.
My background, and caveat lector:
I have been meditating off and on since 1998. I have sat a handful of silent retreats, mostly in the Buddhist "Insight" or "Vipassana" tradition. I have cultivated some amount of mindfulness in my daily life, and I feel that meditation practice (along with lots of psychotherapy) has helped me to achieve a certain amount of ordinary wisdom. However, I am not a meditation teacher, nor an expert on Buddhism (although I have read quite a few books about it!), nor even an advanced practitioner. I have, to my knowledge, never achieved any of the "attainments" (milestones) that some people talk about on the paths of concentration and insight. So, I may or may not be qualified to have an opinion about any of the books listed here. Obviously, I have opinions anyway. :-)
Without further ado… the reviews
Radical Acceptance, by Tara Brach - An introduction to mindfulness (in daily life as well as in formal meditation) with emphasis on acceptance (especially self-acceptance) and equanimity. It’s been a long time since I read this book, but it was instrumental in improving my relationship with meditation, which had previously been characterized by too much striving and self-judgment. It's kind of a hybrid between a self-help book and an introduction to Buddhist mindfulness practice; it's gentle, compassionate and wise. The book includes several basic meditation instructions and would be a great first book for a beginner (or, as it was for me, a nice counterbalance for those trained in more hardcore approaches). Tara Brach also has some guided meditations on her website.
The Mindful Geek, by Michael Taft - An introduction to mindfulness from a very secular perspective (although it’s mostly coming from a Buddhist background, the author’s presentation avoids Buddhist terminology or doctrine). The author approaches meditation from a pragmatic angle, discussing the benefits and what he sees as the main components of practice, including concrete meditation instructions. I really like his description of the three main components of mindfulness practice as concentration, sensory clarity, and acceptance. If you're not interested in Buddhist philosophy and you just want to get to the secular core of mindfulness practice, this book would be a great place to start. A PDF of the book can be found online.
A Path With Heart, by Jack Kornfield - The most comprehensive (yet accessible) overview of the Buddhist path (from a Western perspective) that I know about. The author covers a lot of ground, and while he is rooted in the Theravada (Burmese/Thai) Buddhist tradition, he has a broad, ecumenical perspective on the spiritual path. Kornfield was trained by Burmese and Thai meditation masters and was one of the first Westerners to bring those traditions back to the U.S.; this book retains the meat of the tradition while also being presented in a way that is relatable for present-day Americans. The book is never doctrinaire, but it's definitely a book about spirituality, not about "secular mindfulness". It’s not a detailed meditation manual, but there are bits of meditation instruction sprinkled throughout. Read it if you want to gain a broader (and deeper!) understanding of Buddhism/meditation as a path of wisdom and personal/spiritual growth.
Dancing with Life, by Phillip Moffitt - Organized around the Buddha's "four noble truths", this profound book is really about "suffering and the end of suffering" - and is not really a meditation manual, but rather a guidebook for how our spiritual development might unfold (with the aid of meditation) in terms of our gaining increasing degrees of freedom from suffering. My experience with this book was that I would be reading it, and not really connecting with it, and then out of the blue the author would say something that was exactly what I needed to hear, or which made me feel a bit more “enlightened" just by reading (which is highly unusual in my experience). I suspect the “good bits” would be different for different people (or for the same people at different times). Highly recommended, although I think it would be most helpful to those who already have a bit of meditation experience. (Moffitt's other book, Emotional Chaos to Clarity, is more accessible -- more self-help and less Buddhism -- but also a bit less profound, at least for me personally.)
The Mind Illuminated, by Upasaka Culadasa (John Yates, Ph.D.) - Now this is a meditation manual! Extremely pragmatic meditation guide, containing detailed meditation instructions, written by a Ph.D. neuroscientist who is also a serious Buddhist practitioner. It’s a particular approach, drawing from both Theravada and Tibetan traditions, and it places more emphasis on the development of concentration (versus insight practices) compared to other books on this list, but it’s hard to find books that are as detailed and useful as this one. It uses a stage model, moving from beginning to advanced meditators, and presents detailed instructions specific to each stage. (I’ve only read the first third of the book or so, because after that it gets too advanced for me!) Reading just the first couple of chapters improved my ability to focus when sitting in meditation! So it's a great book for helping you become "better at meditating"... but this can also be a trap: don't let your desire to become a better meditator become a cause of suffering when you feel like it's not working, and remember that meditation can be profoundly useful even when it feels like you're "not doing it right". (Radical Acceptance would be a good book to read first, as a counterbalance to this somewhat attainment-oriented book.)
Happy meditating!