Rental accommodations in Winston-Salem are largely occupied by the student populations who choose to live off-campus. To find an apartment, you need to time your search with the end of the semesters of the school year. November-December and April-May are good times to look, whereas January-February and September-October are much more difficult.
Make sure you shop in the neighborhood that is closest to the school or workplace you need to commute to the most often. With so many schools and big employers in the area, landlords often give preference to those who need to work or study in the immediate area. Doing your homework about the layout of the city before you move is advised.
There is a small, local bus line in Winston-Salem. This is helpful for getting between the main districts of town, but in any particular neighborhood you should have no problem getting everywhere you need to on foot. The time when its best to have a car is if you like to get out of town on a regular basis, as transit to those areas is not nearly as readily available.
Head to the West End to see the most historic buildings and streets in town, and to enjoy the best shopping and dining in the city. If you have a car, head out of the city to explore one of the many wineries in the nearby region. There are also a surprising number of galleries and museums in town, and you can spend many weekends exploring the city's cultural legacy.