Jenny Holiday Books in Order (Updated February 27, 2026)

Jenny Holiday writes both contemporary romance and historical romance, and she tends to organize her books into clear “worlds” (series) plus a smaller set of true standalones.

If you want the smoothest experience, pick a world and read it in order, especially in her contemporary series, where friend groups and past relationships keep popping up.

A quick way to choose your starting book

• Want contemporary small-town romance with a beachy, matchmaking setup? Start with Mermaid Inn (2020).
• Want contemporary romcom with weddings and a tight friend-group vibe? Start with One and Only (2018).
• Want royal/holiday contemporary romance (Eldovia)? Start with A Princess for Christmas (2020).
• Want historical “bromance in Regency clothing” energy? Start with Earls Trip (2024).
• Want a standalone sampler before committing to any series? Try Canadian Boyfriend (2024).

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Contemporary romance series

Matchmaker Bay (read in order)

A coastal setting where community history and prior entanglements are part of the fun, order keeps reveals and cameos clean.

1. Mermaid Inn (2020): A return-to-a-complicated-place setup that rebuilds a career and a heart at the same time, introducing the town’s core emotional knots.
2. Paradise Cove (2020): A second spotlight romance that widens the social web and turns “local history” into active pressure on the relationship.
3. Sandcastle Beach (2021): A later entry that pays off the found-family vibe, where the town itself feels like it’s choosing sides.

Bridesmaids Behaving Badly (read in order, including novellas)

This is a wedding-adjacent friend-group series; reading out of order can spoil who ends up with whom.

0.5. Once Upon a Bride (2018): A quick bridge into the friend group that sets up emotional baggage and who’s been circling whom.

1. One and Only (2018): The series’ launch point, big event energy, big feelings, and a romance that forces the first major reshuffle of the group dynamic.
2. It Takes Two (2018): A relationship-in-motion book where the friendship circle tightens and the romantic stakes become more public.
   2.5. Merrily Ever After (2018): A holiday-side-step that rewards readers already invested in the crew, with cozy momentum and continuity nods.
3. Three Little Words (2019): The payoff-style closer where long-running tension finally has to pick a lane.

A Famous Novel (read in order)

A shorter contemporary pair where public image and private reality collide.

1. Famous (2017): A spotlight romance that sets the series tone: glossy surface, messy feelings underneath, and a heroine learning what she’ll actually tolerate.
2. Infamous (2018): The follow-up that raises the consequences of attention, turning “reputation” into a genuine romantic obstacle.

New Wave Newsroom (read in order)

A compact, workplace-forward series where colleagues and rivals crisscross in ways that make order worthwhile.

1. The Fixer (2016): A career-and-chemistry opener that establishes the newsroom’s pecking order and the first major romantic fault line.
2. The Gossip (2016): A second romance that weaponizes information and forces characters to rethink who they trust.
3. The Pacifist (2016): A resolution-leaning entry where the emotional stakes get quieter but the commitments get harder.

49th Floor (read in order)

A corporate-romance sequence with recurring characters and escalating interconnected drama.

1. Saving the CEO (2014): A power-and-vulnerability opener that sets the workplace tone and the series’ “feelings are a liability” tension.
2. Sleeping with Her Enemy (2015): A romance built on friction and history, where the conflict isn’t just chemistry, it’s consequences.
3. The Engagement Game (2015): A high-concept setup that forces proximity and performance, pushing the series toward bigger, messier stakes.
4. May the Best Man Win (2016): A capstone-style entry (also published under the title His Heart’s Revenge) where earlier rivalries and loyalties come due.

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Historical romance series

Regency Reformers (read in order)

A short historical set where each story stands on its own, but reading in order keeps recurring characters and context consistent.

1. The Miss Mirren Mission (2015): A lively opener that introduces the series’ reform-minded energy and a heroine whose agency drives the romance.
2. The Likelihood of Lucy (2015): A second story that leans into social constraint vs. personal truth, with stronger emotional “earned trust” beats.
3. Viscountess of Vice (2016): A later entry where reputation and reinvention become the central romantic battleground.

Earls Trip (read in order)

A more modern-feeling historical series about longtime friends (earls) on an annual trip, order matters for the evolving friend-group dynamic.

1. Earls Trip (2024): The series doorway, friendship-first chaos plus a romance that tests whether loyalty can survive change.
2. Manic Pixie Dream Earl (2025): A second trip that deepens the emotional undercurrents and makes “this is who I am” impossible to dodge.
3. Brown-Eyed Earl (2026): The next installment, designed to land best once you’ve watched the group dynamic shift across the first two books.

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Holiday royals

Christmas in Eldovia (read in order)

These are contemporary holiday romances in the same fictional royal world. Read in order for setting continuity and recurring characters.

1. A Princess for Christmas (2020): A modern fairytale setup where culture clash and class expectations sharpen the romance.
2. Duke, Actually (2021): A sequel-with-new-couple that expands the royal circle and raises the pressure of public scrutiny.
3. So This Is Christmas (2022): A later holiday entry that leans into tradition, family, and the “choose your future” crescendo.

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Standalones and single-lane reads

These can be read anytime without series prerequisites.

• Undue Influence (2018): A Persuasion-inspired retelling where old wounds and pride complicate second chances, built for readers who like Austen-flavored emotional tension.
• Canadian Boyfriend (2024): A contemporary romance with travel/fresh-start energy, designed as an easy entry point without any series homework.
• Into the Woods (2025): A later-career standalone that leans into personal growth and the risk of wanting something bigger than your current life.
• Book Club Boyfriend (2026): A newer standalone positioned as a modern romcom with public-facing pressure and a relationship that refuses to stay “just for show.”

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If you want one “do this and you’re set” plan

1. Mermaid Inn (2020) → continue Matchmaker Bay in order.
2. One and Only (2018) → continue Bridesmaids Behaving Badly in order (including novellas).
3. A Princess for Christmas (2020) → continue Eldovia in order when you want holiday-only reading.
4. Earls Trip (2024) → continue for historical, friend-group-forward fun.
5. Drop the standalones anywhere as palate cleansers.

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Latest status

Most recent Jenny Holiday novel listed with a 2026 release: Book Club Boyfriend (2026).
Next/other 2026 entry in an ongoing series: Brown-Eyed Earl (2026) (Earls Trip Book 3).