| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Winona | 1 | 26,654 | 25,981 | 0.47% | 1,400 | 19 | City |
| Goodview | 2 | 4,119 | 4,111 | -0.07% | 1,858 | 2 | City |
| St. Charles | 3 | 4,100 | 4,030 | 0.24% | 1,077 | 4 | City |
| Lewiston | 4 | 1,510 | 1,524 | -0.26% | 1,194 | 1 | City |
| Stockton | 5 | 839 | 827 | 0.24% | 494 | 2 | City |
| Rollingstone | 6 | 707 | 680 | 0.57% | 1,625 | 0 | City |
| Altura | 7 | 462 | 465 | -0.22% | 155 | 3 | City |
| Dakota | 8 | 287 | 290 | -0.35% | 518 | 1 | City |
| Utica | 9 | 272 | 278 | -0.73% | 276 | 1 | City |
| Minnesota City | 10 | 187 | 191 | -0.53% | 754 | 0 | City |
Winona is the largest city in Winona County, with a population of 26,654.
Minnesota City is the smallest city in Winona County, with a population of 187.
There are 10 cities in Winona County, Minnesota.