Games like Holiday with Gwen
Games like Holiday with Gwen include Florence, LoveChoice, Tails Noir, The Hungry Lamb: Traveling in the Late Ming Dynasty, and Lay a Beauty to Rest: The Darkness Peach Blossom Spring. We matched them by the tags players give Holiday with Gwen on Steam (Adventure, Casual, Interactive Fiction, Romance, and Detective): closest matches first, and among equally close ones the better-known games.

Florence
Shared: Casual · Adventure · Romance

LoveChoice
Shared: Romance · Dating Sim · Visual Novel

Tails Noir
Shared: Adventure · Detective · Interactive Fiction

The Hungry Lamb: Traveling in the Late Ming Dynasty
Shared: Interactive Fiction · Visual Novel · Adventure

Lay a Beauty to Rest: The Darkness Peach Blossom Spring
Shared: Adventure · Interactive Fiction · Visual Novel

Coffee Talk
Shared: Dialogue Heavy · Interactive Fiction · Visual Novel

Senren * Banka
Shared: Visual Novel · Casual · Dating Sim

Love Is All Around
Shared: Romance · Dating Sim · Visual Novel

The Mermaid Mask
Shared: Adventure · Detective · Interactive Fiction

The Wolf Among Us
Shared: Adventure · Detective · Story Rich

ATRI -My Dear Moments-
Shared: Visual Novel · Romance · Casual

Until Then
Shared: Interactive Fiction · Visual Novel · Romance

Her Story
Shared: Interactive Fiction · Detective · Investigation

Vampires' Melody
Shared: Casual · Adventure · Interactive Fiction

Phoenix Wright: Ace Attorney Trilogy
Shared: Detective · Visual Novel · Adventure

Trials of Innocence
Shared: Interactive Fiction · Detective · Visual Novel

L.A. Noire
Shared: Adventure · Detective · Crime

I Wani Hug that Gator!
Shared: Romance · Visual Novel · Interactive Fiction

Aokana - Four Rhythms Across the Blue
Shared: Casual · Adventure · Romance

Tricolour Lovestory
Shared: Visual Novel · Casual · Dating Sim

To the Moon
Shared: Adventure · Interactive Fiction · Story Rich

No Case Should Remain Unsolved
Shared: Interactive Fiction · Adventure · Visual Novel

Best Served Cold
Shared: Detective · Visual Novel · Interactive Fiction

Duck Detective: The Secret Salami
Shared: Casual · Detective · Adventure