46 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Hartford town | 1 | 10,693 | 10,695 | -0.23% | 237 | 45.11 | Town |
| Springfield town | 2 | 9,007 | 9,065 | -0.34% | 183 | 49.21 | Town |
| Wilder | 3 | 4,120 | 3,146 | 4.09% | 1,619 | 2.54 | CDP |
| Springfield | 4 | 3,938 | 4,028 | -0.05% | 1,178 | 3.34 | CDP |
| Norwich town | 5 | 3,635 | 3,614 | -0.11% | 82 | 44.49 | Town |
| Windsor town | 6 | 3,526 | 3,550 | -0.34% | 182 | 19.41 | Town |
| Hartland town | 7 | 3,498 | 3,450 | 0.2% | 77 | 45.23 | Town |
| Woodstock town | 8 | 3,020 | 3,007 | -0.2% | 69 | 44.05 | Town |
| Chester town | 9 | 3,008 | 2,985 | 0% | 54 | 55.71 | Town |
| White River Junction | 10 | 2,886 | 2,528 | 1.41% | 1,235 | 2.34 | CDP |
| Weathersfield town | 11 | 2,841 | 2,836 | -0.21% | 65 | 43.51 | Town |
| Royalton town | 12 | 2,778 | 2,747 | 0.14% | 69 | 40.37 | Town |
| Ludlow town | 13 | 2,177 | 2,170 | -0.14% | 63 | 34.75 | Town |
| Windsor | 14 | 2,156 | 2,042 | 0.28% | 1,750 | 1.23 | CDP |
| Bethel town | 15 | 1,922 | 1,942 | -0.36% | 42 | 45.50 | Town |
| Sharon town | 16 | 1,568 | 1,562 | -0.06% | 39 | 39.81 | Town |
| Cavendish town | 17 | 1,408 | 1,390 | 0.14% | 36 | 39.40 | Town |
| West Windsor town | 18 | 1,383 | 1,350 | 0.36% | 56 | 24.72 | Town |
| Chester | 19 | 1,120 | 1,023 | 0.72% | 682 | 1.64 | CDP |
| Rochester town | 20 | 1,084 | 1,097 | -0.46% | 19 | 56.84 | Town |
| Barnard town | 21 | 1,020 | 993 | 0.59% | 21 | 48.03 | Town |
| Pomfret town | 22 | 977 | 911 | 1.35% | 25 | 39.48 | Town |
| Woodstock | 23 | 937 | 936 | 0% | 794 | 1.18 | Village |
| Bridgewater town | 24 | 919 | 909 | 0.11% | 19 | 49.48 | Town |
| Norwich | 25 | 829 | 621 | -0.36% | 571 | 1.45 | CDP |
| Ludlow | 26 | 792 | 784 | 0.25% | 592 | 1.34 | Village |
| Stockbridge town | 27 | 739 | 716 | 0.41% | 16 | 45.78 | Town |
| Reading town | 28 | 691 | 687 | 0% | 17 | 41.09 | Town |
| Bethel | 29 | 690 | 891 | 1.17% | 362 | 1.91 | CDP |
| Hartland | 30 | 686 | 537 | 3% | 631 | 1.09 | CDP |
| Plymouth town | 31 | 663 | 640 | 1.07% | 14 | 48.17 | Town |
| Weston town | 32 | 627 | 626 | -0.16% | 18 | 35.37 | Town |
| Hartford Village | 33 | 599 | 334 | 7.16% | 512 | 1.17 | CDP |
| Andover town | 34 | 585 | 567 | 0.52% | 20 | 28.85 | Town |
| West Woodstock | 35 | 496 | 164 | 7.13% | 593 | 0.84 | CDP |
| North Hartland | 36 | 444 | 274 | 2.07% | 443 | 1 | CDP |
| South Royalton | 37 | 420 | 609 | -4.11% | 378 | 1.11 | CDP |
| North Springfield | 38 | 416 | 740 | -2.35% | 338 | 1.23 | CDP |
| Ascutney | 39 | 401 | 380 | -2.2% | 238 | 1.69 | CDP |
| Proctorsville | 40 | 335 | 287 | -2.33% | 412 | 0.81 | CDP |
| Rochester | 41 | 295 | 247 | -0.34% | 465 | 0.63 | CDP |
| Quechee | 42 | 261 | 369 | -9.06% | 141 | 1.85 | CDP |
| Baltimore town | 43 | 234 | 229 | 0.43% | 49 | 4.75 | Town |
| Cavendish | 44 | 215 | 184 | 0.94% | 256 | 0.84 | CDP |
| Weston | 45 | 49 | 33 | 6.52% | 263 | 0.19 | CDP |
| South Woodstock | 46 | 30 | 107 | 7.14% | 33 | 0.92 | CDP |
Hartford town is the largest city in Windsor County, with a population of 10,693.
South Woodstock is the smallest city in Windsor County.
There are 46 cities in Windsor County, Vermont.