Very Holiday Books in Order

The Very Holiday series does exactly what the name promises. These are holiday romances, but they are not one-note seasonal gimmicks. The books are connected by a recurring cast, family chaos, and a mood that stays bright, flirty, and a little ridiculous in the best way. Kayley Loring uses each holiday as a built-in pressure cooker, which means there are always expectations, travel plans, awkward reunions, and too many feelings packed into too few days.

It starts with A Very Bossy Christmas, still the obvious gateway into the series. That book introduces Declan and Maddie, plus the wider group energy that gives the series its shape. The setup has fake-dating tension, boss-and-employee complications, and a family visit that makes it impossible for anyone to stay emotionally detached for long. It is festive, sexy, and very funny, which is why so many readers treat it as the defining book of the set.

From there, the series branches out while staying connected. A Very Friendly Valentine's Day follows Eddie and Birdie, and A Very Vegas St. Patrick's Day hands the spotlight to Nolan and Cora. Both keep the same love of sharp dialogue and relationship chaos, but each holiday shifts the mood a little. Valentine's Day pushes the friendship and longing angle. Vegas on St. Patrick's Day leans into excess, celebration, and quick decisions that may or may not be very smart.

Then A Very Grumpy Father's Day circles back to Declan and Maddie, which helps the series feel less like a stack of unrelated standalones and more like an ongoing hangout with people you already know. After that, A Very No Strings Halloween gives Billy and Donna their turn, and A Very Snowed In New Year brings Holden and Piper into a classic forced-proximity winter setup.

Piper matters even beyond her own book. She is one of the recurring threads that makes the whole series feel personal and funny instead of just theme-based. The same goes for the wider family and friend network, especially the Irish-Italian energy the series keeps coming back to. There are toasts, running jokes, meddling, and enough affection underneath the teasing to make the whole world feel warm.

These books are holiday comfort reads, but not syrupy ones.

The humor is quick, the steam is real, and the characters are allowed to be a little dramatic because, honestly, holidays make almost everyone dramatic. If you want a romance series where each entry can match a different mood and season while still feeling like part of one larger universe, this is a good one to settle into. Start with A Very Bossy Christmas, then read forward and enjoy watching the same circle keep finding new ways to complicate its own love life.