| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Rutland | 1 | 15,297 | 15,794 | -0.43% | 2,025 | 8 | City |
| Castleton | 2 | 4,393 | 4,430 | -0.41% | 113 | 39 | Town |
| Brandon | 3 | 4,235 | 4,125 | 1.49% | 107 | 40 | Town |
| Rutland | 4 | 3,825 | 3,921 | -1.14% | 201 | 19 | Town |
| Poultney | 5 | 2,938 | 3,010 | -0.81% | 69 | 43 | Town |
| Pittsford | 6 | 2,838 | 2,877 | -0.73% | 66 | 43 | Town |
| Fair Haven | 7 | 2,651 | 2,730 | -0.93% | 151 | 18 | Town |
| Clarendon | 8 | 2,390 | 2,393 | -0.33% | 76 | 31 | Town |
| West Rutland | 9 | 2,176 | 2,210 | -1.09% | 121 | 18 | Town |
| Wallingford | 10 | 2,058 | 2,128 | -1.06% | 48 | 43 | Town |
| Proctor | 11 | 1,669 | 1,739 | -1.07% | 225 | 7 | Town |
| Killington | 12 | 1,379 | 1,401 | -0.58% | 29 | 47 | Town |
| Pawlet | 13 | 1,369 | 1,417 | -0.8% | 32 | 43 | Town |
| Mount Holly | 14 | 1,358 | 1,389 | -1.09% | 28 | 49 | Town |
| Danby | 15 | 1,259 | 1,287 | -1.1% | 30 | 42 | Town |
| Chittenden | 16 | 1,203 | 1,235 | -0.99% | 17 | 73 | Town |
| Wells | 17 | 1,182 | 1,210 | -1.09% | 53 | 22 | Town |
| Mendon | 18 | 1,166 | 1,159 | -0.09% | 31 | 38 | Town |
| Shrewsbury | 19 | 1,083 | 1,100 | -0.82% | 22 | 50 | Town |
| Poultney | 20 | 1,070 | 1,090 | -0.19% | 1,701 | 1 | Village |
| Benson | 21 | 958 | 968 | -0.21% | 22 | 44 | Town |
| Middletown Springs | 22 | 775 | 794 | -1.15% | 34 | 23 | Town |
| Hubbardton | 23 | 717 | 734 | -0.97% | 26 | 27 | Town |
| Tinmouth | 24 | 561 | 549 | 0.72% | 20 | 29 | Town |
| Sudbury | 25 | 542 | 543 | -0.37% | 25 | 21 | Town |
| Pittsfield | 26 | 491 | 503 | -1.01% | 24 | 20 | Town |
| Ira | 27 | 376 | 384 | -1.05% | 17 | 22 | Town |
| West Haven | 28 | 243 | 240 | -0.41% | 9.0 | 28 | Town |
| Mount Tabor | 29 | 202 | 206 | -0.98% | 5.0 | 44 | Town |
Rutland is the largest city in Rutland County, with a population of 15,297.
Mount Tabor is the smallest city in Rutland County, with a population of 202.
There are 29 cities in Rutland County, Vermont.