47 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Rutland | 1 | 15,526 | 15,785 | -0.33% | 2,056 | 7.55 | City |
| Castleton town | 2 | 4,436 | 4,446 | -0.07% | 114 | 38.94 | Town |
| Brandon town | 3 | 4,096 | 4,121 | -0.12% | 103 | 39.73 | Town |
| Rutland town | 4 | 3,944 | 3,917 | 0.23% | 207 | 19.05 | Town |
| Poultney town | 5 | 3,015 | 3,023 | -0.03% | 71 | 42.56 | Town |
| Pittsford town | 6 | 2,890 | 2,878 | 0.1% | 67 | 43.29 | Town |
| Fair Haven town | 7 | 2,699 | 2,730 | -0.3% | 154 | 17.51 | Town |
| Fair Haven | 8 | 2,460 | 2,273 | 0.49% | 913 | 2.69 | CDP |
| Clarendon town | 9 | 2,413 | 2,397 | 0.12% | 77 | 31.29 | Town |
| West Rutland | 10 | 2,272 | 2,072 | 0.75% | 618 | 3.68 | CDP |
| West Rutland town | 11 | 2,176 | 2,211 | -0.41% | 121 | 18.03 | Town |
| Wallingford town | 12 | 2,091 | 2,129 | -0.48% | 49 | 42.51 | Town |
| Proctor | 13 | 2,065 | 1,386 | 7.16% | 561 | 3.68 | CDP |
| Brandon | 14 | 1,910 | 1,552 | 0.9% | 675 | 2.83 | CDP |
| Proctor town | 15 | 1,706 | 1,739 | -0.41% | 230 | 7.42 | Town |
| Killington town | 16 | 1,418 | 1,410 | 0.21% | 30 | 47.33 | Town |
| Mount Holly town | 17 | 1,400 | 1,391 | 0.21% | 29 | 49.10 | Town |
| Pawlet town | 18 | 1,390 | 1,417 | -0.43% | 32 | 42.84 | Town |
| Danby town | 19 | 1,299 | 1,284 | 0.39% | 31 | 41.54 | Town |
| Chittenden town | 20 | 1,224 | 1,232 | -0.08% | 17 | 72.73 | Town |
| Wells town | 21 | 1,219 | 1,210 | 0.25% | 55 | 22.34 | Town |
| Mendon town | 22 | 1,160 | 1,158 | -0.26% | 31 | 37.96 | Town |
| Shrewsbury town | 23 | 1,103 | 1,094 | 0.27% | 22 | 50.06 | Town |
| Poultney | 24 | 1,100 | 1,095 | 0.09% | 1,749 | 0.63 | Village |
| Castleton Four Corners | 25 | 975 | 674 | 7.14% | 458 | 2.13 | CDP |
| Benson town | 26 | 957 | 972 | -0.52% | 22 | 43.88 | Town |
| Middletown Springs town | 27 | 794 | 791 | 0.13% | 35 | 22.70 | Town |
| Wallingford | 28 | 775 | 1,029 | -0.51% | 435 | 1.78 | CDP |
| Castleton | 29 | 760 | 1,141 | -5.94% | 602 | 1.26 | CDP |
| Hubbardton town | 30 | 732 | 733 | 0% | 27 | 27.22 | Town |
| Killington Village | 31 | 585 | 445 | 7.14% | 98 | 5.94 | CDP |
| Tinmouth town | 32 | 559 | 550 | 0.36% | 20 | 28.59 | Town |
| Sudbury town | 33 | 545 | 542 | 0% | 25 | 21.39 | Town |
| Pittsford | 34 | 544 | 554 | -2.33% | 275 | 1.98 | CDP |
| North Clarendon | 35 | 530 | 447 | 7.07% | 397 | 1.33 | CDP |
| Pittsfield town | 36 | 503 | 503 | 0% | 25 | 20.48 | Town |
| Pawlet | 37 | 379 | 219 | 7.06% | 149 | 2.54 | CDP |
| West Pawlet | 38 | 376 | 285 | 7.12% | 720 | 0.52 | CDP |
| Ira town | 39 | 373 | 370 | 0.27% | 17 | 22.26 | Town |
| Wells | 40 | 362 | 448 | -0.55% | 456 | 0.79 | CDP |
| East Poultney | 41 | 319 | 260 | 7.05% | 412 | 0.78 | CDP |
| West Haven town | 42 | 246 | 241 | 0.41% | 9 | 28.12 | Town |
| Danby | 43 | 223 | 219 | 7.21% | 312 | 0.71 | CDP |
| Benson | 44 | 213 | 259 | -2.74% | 55 | 3.87 | CDP |
| Mount Tabor town | 45 | 213 | 210 | 0.47% | 5 | 44.11 | Town |
| Chittenden | 46 | 195 | 110 | 7.14% | 396 | 0.49 | CDP |
| Middletown Springs | 47 | 191 | 117 | 7.3% | 275 | 0.69 | CDP |
Rutland is the largest city in Rutland County, with a population of 15,526.
Middletown Springs is the smallest city in Rutland County.
There are 47 cities in Rutland County, Vermont.