Hilderbrand often sets her books in Nantucket, drawing on its unique charm, history, and rhythms to anchor her novels in a vivid sense of place. In Winter Stroll, Nantucket is both the physical setting and a symbolic presence, embodying both comfort and tension for the Quinn family. It reflects the duality of home as a source of stability while also becoming a space where unresolved conflicts surface. The island is the gathering point when everything else in the Quinn family’s lives falls apart. The Winter Street Inn, in particular, is the glue holding the often dysfunctional family together. Every Christmas, no matter the crises they face—Kelley’s wife’s infidelity, Bart fighting in Afghanistan, or his children grappling with personal challenges—the Quinns return to the inn. Nantucket is larger than any individual disaster; it is a constant, a place that remains unchanged even as their lives shift dramatically.

Nantucket also works for the novel’s genre, offering a cozy, festive atmosphere for readers that contrasts with the family’s personal upheavals. The novel’s descriptions capture the island’s physical beauty and seasonal transformation, rendering a cinematic winter landscape that mirrors the heightened emotions of the holidays. The inn, the point, and the town’s main street ground moments of tension, regret, and reconciliation between the characters, tying abstract emotional experience to the concrete environment. Even outsiders like Drake, “fall in love” and become “pretty smitten” (112) with the cozy island. The traditional, quaint New England charm establishes a space where enduring family values matter, even as the Quinns navigate modern challenges such as infidelity, blended family dynamics, and substance use.