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<i>Gastrochilus</i> is an orchid genus containing about 70 species in tropical and subtropical Asia with high morphological diversity. The phylogenetic relationships among this genus have not been fully resolved, and the plastome evolution has not been investigated either. In this study, five plastomes of <i>Gastrochilus</i> were newly reported, and sixteen plastomes of <i>Gastrochilus</i> were used to conduct comparative and phylogenetic analyses. Our results showed that the <i>Gastrochilus</i> plastomes ranged from 146,183 to 148,666 bp, with a GC content of 36.7–36.9%. There were 120 genes annotated, consisting of 74 protein-coding genes, 38 tRNA genes, and 8 rRNA genes. No contraction and expansion of IR borders, gene rearrangements, or inversions were detected. Additionally, the repeat sequences and codon usage bias of <i>Gastrochilus</i> plastomes were highly conserved. Twenty hypervariable regions were selected as potential DNA barcodes. The phylogenetic relationships within <i>Gastrochilus</i> were well resolved based on the whole plastome, especially among main clades. Furthermore, both molecular and morphological data strongly supported <i>Haraella retrocalla</i> as a member of <i>Gastrochilus</i> (<i>G. retrocallus</i>).