Object retrieval skills requiring means-end exploration are delayed or impaired in infants with Down Syndrome (DS). The current study examined the role of ecological constraints, i.e., task difficulty and environmental context on the object retrieval skills of young children with DS. Thirteen children with DS (31.55 ± 4.14 months) and 13 mental-age matched Typically Developing (TD) children (17.31 ± 1.64 months) completed three tasks involving retrieving a toy from a transparent box (task 1), an opaque box (task 2), and a transparent box hidden inside an opaque box (task 3). Both DS and TD group performed similarly for the simpler task 1; but for task 2 and task 3, the DS group had less success rate, fewer use of complex asymmetric hand actions, and/or longer planning and execution times compared to TD group. Future studies should examine the developmental trends and specificity of means-ends exploratory behaviors in children with DS.