Place potatoes into a large pot and cover with salted water; bring to a boil. Reduce heat to medium-low and simmer until tender, about 20 minutes. Drain and let potatoes cool.
Place eggs in a saucepan and cover with water. Bring to a boil, remove from heat, and let eggs stand in hot water for 15 minutes. Remove eggs from hot water, cool under cold running water, and peel. Dice the eggs when cool.
Place the bacon in a large skillet and cook over medium-high heat, turning occasionally, until evenly browned, about 10 minutes. Drain the bacon slices on paper towels. When cooled, crumble and set aside.
Dice potatoes into a large salad bowl and mix with crumbled bacon, diced eggs, and salad dressing. Sprinkle top of salad with shredded Cheddar cheese, and mix the salad thoroughly. Season with black pepper. For best flavor, chill salad overnight.