29 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Winona | 1 | 26,061 | 25,981 | 0.06% | 1,369 | 19.03 | City |
| Goodview | 2 | 4,067 | 4,117 | -0.25% | 1,834 | 2.22 | City |
| St. Charles | 3 | 4,046 | 4,023 | 0.12% | 1,063 | 3.81 | City |
| Lewiston | 4 | 1,495 | 1,524 | -0.4% | 1,182 | 1.26 | City |
| Homer township | 5 | 1,309 | 1,295 | 0.31% | 37 | 35.28 | Township |
| Wilson township | 6 | 1,148 | 1,145 | 0% | 33 | 34.34 | Township |
| New Hartford township | 7 | 817 | 809 | 0.37% | 23 | 35.20 | Township |
| Stockton | 8 | 816 | 816 | 0% | 480 | 1.70 | City |
| Hillsdale township | 9 | 789 | 765 | 0.64% | 49 | 16 | Township |
| Rollingstone township | 10 | 782 | 770 | 0.39% | 26 | 29.73 | Township |
| Rollingstone | 11 | 684 | 666 | 0.59% | 1,572 | 0.43 | City |
| St. Charles township | 12 | 658 | 652 | 0.15% | 21 | 31.83 | Township |
| Saratoga township | 13 | 629 | 620 | 0.32% | 18 | 35.74 | Township |
| Utica township | 14 | 581 | 569 | 0.52% | 17 | 33.72 | Township |
| Pleasant Hill township | 15 | 538 | 530 | 0.37% | 15 | 35.72 | Township |
| Norton township | 16 | 531 | 525 | 0.38% | 16 | 32.57 | Township |
| Altura | 17 | 461 | 471 | -0.43% | 155 | 2.98 | City |
| Dresbach township | 18 | 418 | 409 | 0.72% | 53 | 7.87 | Township |
| Wiscoy township | 19 | 356 | 352 | 0.28% | 10 | 35.67 | Township |
| Elba township | 20 | 324 | 325 | -0.31% | 10 | 33.52 | Township |
| Fremont township | 21 | 317 | 310 | 0.63% | 9 | 35.80 | Township |
| Hart township | 22 | 299 | 298 | 0% | 8 | 35.59 | Township |
| Dakota | 23 | 287 | 294 | -0.35% | 518 | 0.55 | City |
| Mount Vernon township | 24 | 279 | 274 | 0.72% | 8 | 35.12 | Township |
| Utica | 25 | 254 | 264 | -0.78% | 257 | 0.99 | City |
| Whitewater township | 26 | 212 | 206 | 0.95% | 6 | 35.22 | Township |
| Minnesota City | 27 | 182 | 186 | -0.55% | 734 | 0.25 | City |
| Pickwick | 28 | 178 | 90 | 7.23% | 277 | 0.64 | CDP |
| Homer | 29 | 118 | 176 | -4.07% | 99 | 1.19 | CDP |
Winona is the largest city in Winona County, with a population of 26,061.
Homer is the smallest city in Winona County.
There are 29 cities in Winona County, Minnesota.