26 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Hartford | 1 | 10,578 | 10,694 | -0.74% | 234 | 45 | Town |
| Springfield | 2 | 8,996 | 9,066 | -0.35% | 183 | 49 | Town |
| Norwich | 3 | 3,614 | 3,614 | -0.36% | 81 | 44 | Town |
| Windsor | 4 | 3,496 | 3,548 | -0.74% | 180 | 19 | Town |
| Hartland | 5 | 3,410 | 3,449 | -0.9% | 75 | 45 | Town |
| Woodstock | 6 | 2,988 | 3,005 | -0.66% | 68 | 44 | Town |
| Chester | 7 | 2,984 | 2,985 | -0.3% | 54 | 56 | Town |
| Weathersfield | 8 | 2,813 | 2,838 | -0.74% | 65 | 44 | Town |
| Royalton | 9 | 2,723 | 2,748 | -0.87% | 67 | 40 | Town |
| Ludlow | 10 | 2,149 | 2,169 | -0.69% | 62 | 35 | Town |
| Bethel | 11 | 1,900 | 1,942 | -0.84% | 42 | 45 | Town |
| Sharon | 12 | 1,547 | 1,564 | -0.83% | 39 | 40 | Town |
| Cavendish | 13 | 1,384 | 1,395 | -0.86% | 35 | 39 | Town |
| West Windsor | 14 | 1,356 | 1,348 | -0.51% | 55 | 25 | Town |
| Rochester | 15 | 1,080 | 1,097 | -0.64% | 19 | 57 | Town |
| Barnard | 16 | 989 | 991 | -0.8% | 21 | 48 | Town |
| Pomfret | 17 | 960 | 913 | 0.42% | 24 | 39 | Town |
| Woodstock | 18 | 924 | 936 | -0.32% | 783 | 1 | Village |
| Bridgewater | 19 | 893 | 903 | -1% | 18 | 49 | Town |
| Ludlow | 20 | 780 | 784 | -0.13% | 583 | 1 | Village |
| Stockbridge | 21 | 725 | 715 | -0.41% | 16 | 46 | Town |
| Reading | 22 | 681 | 684 | -0.44% | 17 | 41 | Town |
| Plymouth | 23 | 653 | 638 | 0.46% | 14 | 48 | Town |
| Weston | 24 | 626 | 628 | -0.32% | 18 | 35 | Town |
| Andover | 25 | 569 | 571 | -1.04% | 20 | 29 | Town |
| Baltimore | 26 | 234 | 231 | 0% | 49 | 5 | Town |
Hartford is the largest city in Windsor County, with a population of 10,578.
Baltimore is the smallest city in Windsor County, with a population of 234.
There are 26 cities in Windsor County, Vermont.