Weatherleah was once the home of the Jemane family, but was ravaged by 3 Redguard Valley Ogres. It lies south of Chorrol, southwest of Hackdirt, and east by southeast of Rock Bottom Caverns. If looking at your map, it is right at the top of the letter L of the "IMPERIAL RESERVES." After reuniting the Jemane brothers, Guilbert asks that you make Weatherleah safe for him and his brother to return to. After ridding the area of Ogres, the brothers return and eventually fix the place up.
There is also a huge amount of Fly Amanita Caps in the area