47 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 |
| Fair Haven | 8 | 2,460 | 2,273 | 0.49% | 913 | 3 | CDP |
| Clarendon | 9 | 2,405 | 2,396 | -0.17% | 77 | 31 | Town |
| West Rutland | 10 | 2,272 | 2,072 | 0.75% | 618 | 4 | CDP |
| West Rutland | 11 | 2,266 | 2,210 | 1.52% | 126 | 18 | Town |
| Wallingford | 12 | 2,094 | 2,129 | -0.52% | 49 | 43 | Town |
| Proctor | 13 | 2,065 | 1,386 | 7.16% | 561 | 4 | CDP |
| Brandon | 14 | 1,910 | 1,552 | 0.9% | 675 | 3 | CDP |
| Proctor | 15 | 1,700 | 1,739 | -0.7% | 229 | 7 | Town |
| Killington | 16 | 1,390 | 1,399 | -0.5% | 29 | 47 | Town |
| Pawlet | 17 | 1,390 | 1,418 | -0.57% | 32 | 43 | Town |
| Mount Holly | 18 | 1,380 | 1,391 | -0.65% | 28 | 49 | Town |
| Danby | 19 | 1,278 | 1,283 | -0.47% | 31 | 42 | Town |
| Chittenden | 20 | 1,222 | 1,232 | -0.24% | 17 | 73 | Town |
| Wells | 21 | 1,202 | 1,209 | -0.5% | 54 | 22 | Town |
| Mendon | 22 | 1,179 | 1,166 | 0.08% | 31 | 38 | Town |
| Shrewsbury | 23 | 1,098 | 1,095 | -0.09% | 22 | 50 | Town |
| Poultney | 24 | 1,091 | 1,093 | -0.09% | 1,734 | 1 | Village |
| Castleton Four Corners | 25 | 975 | 674 | 7.14% | 458 | 2 | CDP |
| Benson | 26 | 961 | 972 | -0.41% | 22 | 44 | Town |
| Middletown Springs | 27 | 789 | 790 | -0.25% | 35 | 23 | Town |
| Wallingford | 28 | 775 | 1,029 | -0.51% | 435 | 2 | CDP |
| Castleton | 29 | 760 | 1,141 | -5.94% | 602 | 1 | CDP |
| Hubbardton | 30 | 730 | 733 | -0.27% | 27 | 27 | Town |
| Killington Village | 31 | 585 | 445 | 7.14% | 98 | 6 | CDP |
| Tinmouth | 32 | 554 | 550 | 0% | 19 | 29 | Town |
| Sudbury | 33 | 545 | 542 | -0.18% | 25 | 21 | Town |
| Pittsford | 34 | 544 | 554 | -2.33% | 275 | 2 | CDP |
| North Clarendon | 35 | 530 | 447 | 7.07% | 397 | 1 | CDP |
| Pittsfield | 36 | 499 | 503 | -0.6% | 24 | 20 | Town |
| Pawlet | 37 | 379 | 219 | 7.06% | 149 | 3 | CDP |
| West Pawlet | 38 | 376 | 285 | 7.12% | 720 | 1 | CDP |
| Ira | 39 | 367 | 370 | -0.54% | 16 | 22 | Town |
| Wells | 40 | 362 | 448 | -0.55% | 456 | 1 | CDP |
| East Poultney | 41 | 319 | 260 | 7.05% | 412 | 1 | CDP |
| West Haven | 42 | 246 | 240 | 0.82% | 9 | 28 | Town |
| Danby | 43 | 223 | 219 | 7.21% | 312 | 1 | CDP |
| Benson | 44 | 213 | 259 | -2.74% | 55 | 4 | CDP |
| Mount Tabor | 45 | 207 | 209 | -0.96% | 5 | 44 | Town |
| Chittenden | 46 | 195 | 110 | 7.14% | 396 | 0 | CDP |
| Middletown Springs | 47 | 191 | 117 | 7.3% | 275 | 1 | CDP |
Rutland is the largest city in Rutland County, with a population of 15,511.
Middletown Springs is the smallest city in Rutland County, with a population of 191.
There are 47 cities in Rutland County, Vermont.