29 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Rutland | 1 | 15,511 | 15,781 | -0.35% | 2,054 | 8 | City |
| Castleton | 2 | 4,461 | 4,445 | 0.13% | 115 | 39 | Town |
| Brandon | 3 | 4,119 | 4,122 | 0.07% | 104 | 40 | Town |
| Rutland | 4 | 3,898 | 3,920 | -0.51% | 205 | 19 | Town |
| Poultney | 5 | 2,983 | 3,010 | -0.4% | 70 | 43 | Town |
| Pittsford | 6 | 2,892 | 2,880 | 0.03% | 67 | 43 | Town |
| Fair Haven | 7 | 2,697 | 2,730 | -0.48% | 154 | 18 | Town |
| Clarendon | 8 | 2,405 | 2,396 | -0.17% | 77 | 31 | Town |
| West Rutland | 9 | 2,266 | 2,210 | 1.52% | 126 | 18 | Town |
| Wallingford | 10 | 2,094 | 2,129 | -0.52% | 49 | 43 | Town |
| Proctor | 11 | 1,700 | 1,739 | -0.7% | 229 | 7 | Town |
| Killington | 12 | 1,390 | 1,399 | -0.5% | 29 | 47 | Town |
| Pawlet | 13 | 1,390 | 1,418 | -0.57% | 32 | 43 | Town |
| Mount Holly | 14 | 1,380 | 1,391 | -0.65% | 28 | 49 | Town |
| Danby | 15 | 1,278 | 1,283 | -0.47% | 31 | 42 | Town |
| Chittenden | 16 | 1,222 | 1,232 | -0.24% | 17 | 73 | Town |
| Wells | 17 | 1,202 | 1,209 | -0.5% | 54 | 22 | Town |
| Mendon | 18 | 1,179 | 1,166 | 0.08% | 31 | 38 | Town |
| Shrewsbury | 19 | 1,098 | 1,095 | -0.09% | 22 | 50 | Town |
| Poultney | 20 | 1,091 | 1,093 | -0.09% | 1,734 | 1 | Village |
| Benson | 21 | 961 | 972 | -0.41% | 22 | 44 | Town |
| Middletown Springs | 22 | 789 | 790 | -0.25% | 35 | 23 | Town |
| Hubbardton | 23 | 730 | 733 | -0.27% | 27 | 27 | Town |
| Tinmouth | 24 | 554 | 550 | 0% | 19 | 29 | Town |
| Sudbury | 25 | 545 | 542 | -0.18% | 25 | 21 | Town |
| Pittsfield | 26 | 499 | 503 | -0.6% | 24 | 20 | Town |
| Ira | 27 | 367 | 370 | -0.54% | 16 | 22 | Town |
| West Haven | 28 | 246 | 240 | 0.82% | 9 | 28 | Town |
| Mount Tabor | 29 | 207 | 209 | -0.96% | 5 | 44 | Town |
Rutland is the largest city in Rutland County, with a population of 15,511.
Mount Tabor is the smallest city in Rutland County, with a population of 207.
There are 29 cities in Rutland County, Vermont.