39 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Cortland | 1 | 17,444 | 17,556 | -0.09% | 4,480 | 4 | City |
| Cortland | 2 | 17,444 | 17,516 | -0.09% | 4,480 | 4 | City |
| Cortlandville | 3 | 8,174 | 8,409 | -0.22% | 164 | 50 | Town |
| Cortlandville | 4 | 8,174 | 8,402 | -0.22% | 164 | 50 | Town |
| Homer | 5 | 6,096 | 6,292 | -0.16% | 121 | 50 | Town |
| Homer | 6 | 6,096 | 6,288 | -0.16% | 121 | 50 | Town |
| Homer | 7 | 3,049 | 3,184 | -0.88% | 1,584 | 2 | Village |
| Homer | 8 | 3,049 | 3,182 | -0.88% | 1,584 | 2 | Village |
| Virgil | 9 | 2,382 | 2,427 | -0.21% | 50 | 47 | Town |
| Virgil | 10 | 2,382 | 2,427 | -0.21% | 50 | 47 | Town |
| Marathon | 11 | 1,962 | 2,038 | -0.41% | 79 | 25 | Town |
| Marathon | 12 | 1,962 | 2,036 | -0.41% | 79 | 25 | Town |
| Preble | 13 | 1,298 | 1,357 | -0.61% | 48 | 27 | Town |
| Preble | 14 | 1,298 | 1,356 | -0.61% | 48 | 27 | Town |
| Scott | 15 | 1,058 | 1,075 | 0.09% | 48 | 22 | Town |
| Scott | 16 | 1,058 | 1,074 | 0.09% | 48 | 22 | Town |
| Solon | 17 | 1,042 | 1,062 | 0.1% | 35 | 30 | Town |
| Solon | 18 | 1,042 | 1,064 | 0.1% | 35 | 30 | Town |
| McGraw | 19 | 968 | 1,012 | -0.92% | 981 | 1 | Village |
| McGraw | 20 | 968 | 1,011 | -0.92% | 981 | 1 | Village |
| Truxton | 21 | 954 | 1,000 | -0.52% | 21 | 45 | Town |
| Truxton | 22 | 954 | 999 | -0.52% | 21 | 45 | Town |
| Cincinnatus | 23 | 890 | 903 | 0.45% | 35 | 25 | Town |
| Cincinnatus | 24 | 890 | 902 | 0.45% | 35 | 25 | Town |
| Cuyler | 25 | 879 | 911 | -0.57% | 20 | 43 | Town |
| Cuyler | 26 | 879 | 910 | -0.57% | 20 | 43 | Town |
| Marathon | 27 | 875 | 915 | -0.91% | 774 | 1 | Village |
| Marathon | 28 | 875 | 914 | -0.91% | 774 | 1 | Village |
| Willet | 29 | 864 | 895 | -0.23% | 34 | 26 | Town |
| Willet | 30 | 864 | 894 | -0.23% | 34 | 26 | Town |
| Harford | 31 | 859 | 875 | -0.12% | 36 | 24 | Town |
| Harford | 32 | 859 | 875 | -0.12% | 36 | 24 | Town |
| Lapeer | 33 | 794 | 794 | 1.28% | 32 | 25 | Town |
| Lapeer | 34 | 794 | 794 | 1.28% | 32 | 25 | Town |
| Freetown | 35 | 756 | 766 | 0% | 30 | 25 | Town |
| Freetown | 36 | 756 | 766 | 0% | 30 | 25 | Town |
| Taylor | 37 | 430 | 448 | -0.46% | 14 | 30 | Town |
| Taylor | 38 | 430 | 448 | -0.46% | 14 | 30 | Town |
| Blodgett Mills | 39 | 200 | 212 | -3.38% | 92 | 2 | CDP |
Cortland is the largest city in Cortland County, with a population of 17,444.
Blodgett Mills is the smallest city in Cortland County, with a population of 200.
There are 39 cities in Cortland County, New York.