29 cities
| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Rutland | 1 | 15,457 | 15,781 | -0.35% | 2,046 | 8 | City |
| Castleton | 2 | 4,467 | 4,445 | 0.13% | 115 | 39 | Town |
| Brandon | 3 | 4,122 | 4,122 | 0.07% | 104 | 40 | Town |
| Rutland | 4 | 3,878 | 3,920 | -0.51% | 204 | 19 | Town |
| Poultney | 5 | 2,971 | 3,010 | -0.4% | 70 | 43 | Town |
| Pittsford | 6 | 2,893 | 2,880 | 0.03% | 67 | 43 | Town |
| Fair Haven | 7 | 2,684 | 2,730 | -0.48% | 153 | 18 | Town |
| Clarendon | 8 | 2,401 | 2,396 | -0.17% | 77 | 31 | Town |
| West Rutland | 9 | 2,300 | 2,210 | 1.5% | 128 | 18 | Town |
| Wallingford | 10 | 2,083 | 2,129 | -0.53% | 49 | 43 | Town |
| Proctor | 11 | 1,688 | 1,739 | -0.71% | 228 | 7 | Town |
| Killington | 12 | 1,383 | 1,399 | -0.5% | 29 | 47 | Town |
| Pawlet | 13 | 1,382 | 1,418 | -0.58% | 32 | 43 | Town |
| Mount Holly | 14 | 1,371 | 1,391 | -0.65% | 28 | 49 | Town |
| Danby | 15 | 1,272 | 1,283 | -0.47% | 31 | 42 | Town |
| Chittenden | 16 | 1,219 | 1,232 | -0.25% | 17 | 73 | Town |
| Wells | 17 | 1,196 | 1,209 | -0.5% | 54 | 22 | Town |
| Mendon | 18 | 1,180 | 1,166 | 0.08% | 31 | 38 | Town |
| Shrewsbury | 19 | 1,097 | 1,095 | -0.09% | 22 | 50 | Town |
| Poultney | 20 | 1,091 | 1,093 | 0% | 1,734 | 1 | Village |
| Benson | 21 | 957 | 972 | -0.42% | 22 | 44 | Town |
| Middletown Springs | 22 | 787 | 790 | -0.25% | 35 | 23 | Town |
| Hubbardton | 23 | 728 | 733 | -0.27% | 27 | 27 | Town |
| Tinmouth | 24 | 554 | 550 | 0% | 19 | 29 | Town |
| Sudbury | 25 | 544 | 542 | -0.18% | 25 | 21 | Town |
| Pittsfield | 26 | 496 | 503 | -0.6% | 24 | 20 | Town |
| Ira | 27 | 365 | 370 | -0.54% | 16 | 22 | Town |
| West Haven | 28 | 248 | 240 | 0.81% | 9 | 28 | Town |
| Mount Tabor | 29 | 205 | 209 | -0.97% | 5 | 44 | Town |
Rutland is the largest city in Rutland County, with a population of 15,457.
Mount Tabor is the smallest city in Rutland County, with a population of 205.
There are 29 cities in Rutland County, Vermont.