Games like Winter Dream
Games like Winter Dream include Volcano Princess, Tricolour Lovestory, ATRI -My Dear Moments-, 小白兔电商~Bunny e-Shop, and LoveChoice. We matched them by the tags players give Winter Dream on Steam (Casual, Simulation, Dating Sim, Interactive Fiction, and Life Sim): closest matches first, and among equally close ones the better-known games.

Volcano Princess
Shared: Life Sim · Dating Sim · Simulation

Tricolour Lovestory
Shared: Dating Sim · Visual Novel · Simulation

ATRI -My Dear Moments-
Shared: Visual Novel · Casual · Dating Sim

小白兔电商~Bunny e-Shop
Shared: Dating Sim · Simulation · Visual Novel

LoveChoice
Shared: Dating Sim · Visual Novel · Simulation

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

Doki Doki Literature Club Plus!
Shared: Dating Sim · Visual Novel · Anime

The Sims™ 4
Shared: Life Sim · Simulation · Dating Sim

Class of '09: The Re-Up
Shared: Visual Novel · Casual · Simulation

Emily is Away <3
Shared: Simulation · Dating Sim · Casual

Gaokao.Love.100Days
Shared: Dating Sim · Simulation · Visual Novel

Lucy -The Eternity She Wished For-
Shared: Dating Sim · Visual Novel · Anime

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

Summer Pockets
Shared: Casual · Visual Novel · Dating Sim

Chinese Parents
Shared: Simulation · Casual · Life Sim

Magical Princess
Shared: Life Sim · Simulation · Dating Sim

School Days
Shared: Dating Sim · Life Sim · Choose Your Own Adventure

STORY OF SEASONS: Friends of Mineral Town
Shared: Simulation · Casual · Dating Sim

Love Is All Around
Shared: Dating Sim · Visual Novel · Interactive Fiction

恋爱绮谭~不存在的夏天~
Shared: Casual · Visual Novel · Interactive Fiction

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

Date Everything!
Shared: Dating Sim · Simulation · Visual Novel

CLANNAD
Shared: Visual Novel · Dating Sim · Anime

Rewrite+
Shared: Casual · Visual Novel · Interactive Fiction