Loess landslide is one of the main geology disasters in the loess area. Loess landslides have closely relation with the seepage of surface water in the loess with fissures. Water may seep along the different directions in loess with fissure. The confining pressure has a big influence on the water seepage in soil, so it is very important to research the properties of water seepage in the loess with fissure in the different directions and the influence of confining pressure on the loess’s permeability. The tri-axial test is used in this paper. Test results demonstrate that (1) velocity of water going forward is different when water seeps along different directions of fissure loess. (2) The permeability of loess has closely relationship with its structure. (3) The seepage of water is slower when water seep vertically with fissure in the loess. (4) The faster the sample is saturated, the bigger growth rate of the sample’s volume strain will be. (5) The saturated hydraulic conductivity of loess is increased with the increase of the confining pressure. The study can provide the reference for the research of surface water seepage along the fissures and loess landslides.