Cover of The Inn at Eagle Point
Cover of Harbor Lights
Cover of Driftwood Cottage
Cover of Moonlight Cove
Cover of Beach Lane
Cover of An O'Brien Family Christmas
Series

Chesapeake Shores

12 books

Here are 12 books from the Chesapeake Shores series by Sherryl Woods. Start with The Inn at Eagle Point (2009), then read the rest in the order below. Books without a series number are listed in publication order.

Books in order

1
Cover of The Inn at Eagle Point

The Inn at Eagle Point

Sherryl Woods

When successful Wall Street financial planner Abby O’Brien returns to her hometown, it is not for a visit—she is determined to save her sister’s struggling inn from foreclosure. Her homecoming draws her into long-standing family tensions and brings her face-to-face with Trace Riley, the man she loved fifteen years ago. As Abby works to protect the inn and repair fractured relationships, she must decide whether the life she built in New York is truly where she belongs. A warm, emotionally resonant story of family loyalty, forgiveness, second chances, and finding the courage to come home.

RomanceContemporary Romance
1

Chesapeake Shores Christmas

Sherryl Woods

Chesapeake Shores Christmas

Sherryl Woods

When divorced financial expert Abby O’Brien Winters returns to Chesapeake Shores for the holidays, she is drawn back into the complicated, loving orbit of her large family. At the center of the season is the long-awaited reunion of her parents, Mick and Megan O’Brien, whose decision to make their marriage official again stirs both celebration and old emotions among their grown children. As Christmas brings the O’Briens together, family tensions, second chances, and the possibility of renewed love take center stage. Warm, engaging, and emotionally rich, this story introduces a close-knit coastal family whose lives are shaped by loyalty, forgiveness, and the enduring bonds of home.

RomanceContemporary Romance
3

Flowers on Main

Sherryl Woods

Flowers on Main

Sherryl Woods

When her latest plays fail and her relationship with her demanding mentor collapses, playwright Bree O’Brien leaves Chicago behind and returns to Chesapeake Shores, hoping that opening Flowers on Main will bring a fresh challenge and a new sense of purpose. But rebuilding her career—and finding peace in her hometown—proves more complicated than expected as old connections, family expectations, and the possibility of love resurface. Set against the warmth and tensions of a close-knit coastal community, this emotionally rich story explores second chances, creative renewal, family bonds, and the courage to begin again.

RomanceContemporary Romance
3
Cover of Harbor Lights

Harbor Lights

Sherryl Woods

Former army medic Kevin O’Brien returns to Chesapeake Shores as a newly single father, seeking stability and a safe haven for his young son after a devastating loss. As he reconnects with his close-knit family and tries to rebuild his life, unexpected challenges—and the possibility of love—force him to confront the past and imagine a new future. Set against the warmth of a coastal community, this emotionally rich story explores grief, healing, family loyalty, and the courage it takes to begin again.

RomanceContemporary Romance
5
Cover of Driftwood Cottage

Driftwood Cottage

Sherryl Woods

When single mother Heather Donovan arrives in Chesapeake Shores, her hopes for a secure home and loving family finally seem within reach. Yet building a new life in a close-knit coastal community brings emotional challenges, unexpected complications, and the need to confront the past. Against a backdrop of small-town charm and family traditions, intertwined romances—including a long-awaited wedding—test the strength of love, forgiveness, and second chances. Heartwarming and character-driven, this story celebrates the enduring bonds of family and the courage it takes to begin again.

RomanceContemporary Romance
6
Cover of Moonlight Cove

Moonlight Cove

Sherryl Woods

In the close-knit coastal community of Chesapeake Shores, a woman who has worked hard to overcome past struggles is determined to build a stable, fulfilling future. But when love and family complications challenge her carefully guarded independence, she must decide whether to risk her heart and trust the people who care about her. Blending heartfelt romance with themes of resilience, second chances, and the enduring bonds of family, this warm, emotionally engaging story celebrates finding hope—and home—where you least expect it.

RomanceContemporary Romance
7
Cover of Beach Lane

Beach Lane

Sherryl Woods

In the close-knit coastal community of Chesapeake Shores, longtime friends Susie O’Brien and Mack Franklin take an unexpected leap that transforms their relationship and their lives. As they begin married life almost overnight, they must navigate the challenges of commitment, family expectations, and the fears that can stand between friendship and lasting love. Set against the warmth and beauty of small-town Maryland, this heartfelt romance celebrates second chances, emotional courage, and the enduring strength of family bonds.

RomanceContemporary Romance
8
Cover of An O'Brien Family Christmas

An O'Brien Family Christmas

Sherryl Woods

The O’Brien family heads to Ireland for a Christmas holiday filled with old memories, lively family gatherings, and emotions that refuse to stay buried. After ending her relationship with Matthew O’Brien, Laila Riley finds herself drawn back into his orbit—and forced to confront the feelings they have both tried to leave behind. Against the warmth and complications of the O’Brien clan, their story explores love, forgiveness, second chances, and the enduring bonds of family. With its festive setting and heartfelt romance, this holiday tale offers the signature warmth and emotional richness of a Chesapeake Shores story.

RomanceContemporary Romance
11
Cover of Willow Brook Road

Willow Brook Road

Sherryl Woods

After returning to Chesapeake Shores with a broken heart and a glamorous fashion career behind her, spirited Carrie Winters finds herself under the watchful eyes of her close-knit family and hometown community. As she considers a new professional direction, Carrie is drawn to Sam Winslow, a grieving man unexpectedly called upon to care for his young nephew. Their growing connection challenges both of them to reconsider what they truly want—and whether love, family, and fresh beginnings can offer the future they have been seeking. Set against the warmth and expectations of the O’Brien family, this heartfelt romance explores second chances, belonging, and the courage to build a life on one’s own terms.

RomanceContemporary RomanceContemporary Fiction
Cover of The Christmas Bouquet

The Christmas Bouquet

Sherryl Woods

At a Christmas wedding, Caitlyn unexpectedly catches the bouquet meant for her twin sister, Carrie—and finds herself facing questions about her own future. As she wrestles with an unplanned pregnancy and the choices ahead, Caitlyn must move beyond denial to consider what she truly wants and where she belongs. Set against the warmth of family, friendship, and small-town life, this emotionally satisfying contemporary romance explores love, responsibility, and the courage to begin again.

RomanceContemporary Romance
Cover of Dogwood Hill

Dogwood Hill

Sherryl Woods

When former professional football quarterback Aidan Mitchell arrives in Chesapeake Shores to coach the local high school team, the close-knit town quickly welcomes him into its fold. He is drawn to a woman determined to rebuild her life and leave past heartache behind, but starting over proves complicated in a community where family ties and old histories run deep. Set against the warmth and bustle of small-town life, this contemporary romance explores second chances, belonging, trust, and the courage to open one’s heart again.

RomanceContemporary Romance
Cover of Lilac Lane

Lilac Lane

Sherryl Woods

After raising three children on her own following the collapse of her first marriage, Keira Malone has devoted herself to family and carefully protected her heart. But when a new romance brings unexpected chemistry and emotional sparks, she must decide whether she is ready to risk love again. Set against the warm, close-knit community of Chesapeake Shores, this sweet, clean romance celebrates second chances, enduring family bonds, and the healing power of belonging.

RomanceContemporary Romance