This paper intends to explore strategies of cultural translation and their conditioning factors based on the contrastive study of the two English versions of Hong Lou Meng, Yang Hsien-yi and Gladys Yang’s A Dream of Red Mansions and David Hawkes’ The Story of the Stone. Part 1 presents the two versions’ different treatment of the original cultural messages in the novel such as the colour word 㓒(red), the animal words 嗉(dragon) and phoenix, the religious word 血ԉ(immortal), the culinary words ㊣(rice), 依(meal), ⻇(bowl) and 䬵(pan), the ethical expressions (three obediences and four virtues), arrogance and insolence, wifeliness, rhetorical devices and aesthetic concepts. Part 2 analyses their distinct translating strategies and the factors conditioning them. The Yangs’ version prefers literal translation while the Hawkes’ free translation; the former emphasises the rendition of meaning and the latter the production of effect; the former prioritises ‘cultural facsimile’ and the latter ‘cultural adaptation’.