With the increasing contradictions between the limited waste disposal capacity and the vast generation of construction and demolition waste, the cross-regional disposal strategies for the waste have been adopted by some cities to alleviate the local waste management pressure. However, so far there is very limited knowledge regarding the collaborative mechanism for promoting cross-regional waste management. As an “up-to-bottom” approach, the system dynamics approach has been used extensively for investigating complex and dynamic systems and is capable of simulating the dynamic interactions of key driving factors in collaborative management of the cross-regional waste. Hence, a system dynamics model was built to evaluate measures that could promote the cross-regional collaborative management of the waste. The results indicate that a reasonable landfill charging scheme considering landfilling capacity helps to increase the efficiency of cross-regional collaborative management. Particularly, when the landfilling capacity is insufficient, a landfill fee at 95 yuan/ton could minimize the illegal dumping activities in regions involving the waste cross-regional mobility. While if the landfilling capacity is sufficient, the landfill fee could be adjusted from 95 yuan/ton to 70 yuan/ton. Finally, five recommendations have been proposed to improve the cross-regional collaborative waste management policies, which are: 1) unifying waste treatment standards, 2) defining cross-regional waste management decisions, 3) establishing dynamic penalty mechanisms, 4) optimizing the landfill charging scheme, and 5) facilitating collaborative waste management mechanisms. The findings provide suggestions for the waste disposal enterprises to make decisions on cross-regional disposal and suggest approaches for government departments to promote practices of cross-regional collaborative management of the waste.