42 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Brattleboro town | 1 | 12,084 | 12,166 | -0.11% | 377 | 32.06 | Town |
| Brattleboro | 2 | 7,575 | 6,429 | 0.15% | 1,804 | 4.20 | CDP |
| Rockingham town | 3 | 4,777 | 4,833 | -0.19% | 115 | 41.41 | Town |
| Westminster town | 4 | 3,014 | 3,002 | 0.1% | 67 | 45.02 | Town |
| West Brattleboro | 5 | 2,836 | 3,042 | 0.21% | 1,735 | 1.64 | CDP |
| Bellows Falls | 6 | 2,755 | 2,789 | -0.25% | 2,027 | 1.36 | Village |
| Putney town | 7 | 2,600 | 2,614 | -0.19% | 98 | 26.66 | Town |
| Wilmington town | 8 | 2,294 | 2,251 | 0.44% | 57 | 40.45 | Town |
| Vernon town | 9 | 2,209 | 2,180 | 0.36% | 114 | 19.45 | Town |
| Guilford town | 10 | 2,141 | 2,122 | 0.28% | 54 | 39.55 | Town |
| Londonderry town | 11 | 1,953 | 1,917 | 0.57% | 55 | 35.47 | Town |
| Dummerston town | 12 | 1,896 | 1,863 | 0.37% | 62 | 30.70 | Town |
| Dover town | 13 | 1,867 | 1,799 | 0.76% | 52 | 35.77 | Town |
| Marlboro town | 14 | 1,798 | 1,725 | 0.9% | 45 | 40.35 | Town |
| Newfane town | 15 | 1,656 | 1,643 | 0% | 42 | 39.76 | Town |
| Whitingham town | 16 | 1,370 | 1,339 | 0.51% | 37 | 36.76 | Town |
| Townshend town | 17 | 1,303 | 1,289 | 0.31% | 31 | 42.28 | Town |
| Jamaica town | 18 | 1,009 | 998 | 0.4% | 21 | 48.95 | Town |
| Wardsboro town | 19 | 869 | 867 | 0.12% | 30 | 29.22 | Town |
| Halifax town | 20 | 759 | 776 | -0.52% | 19 | 39.72 | Town |
| Grafton town | 21 | 648 | 643 | 0.31% | 17 | 38.14 | Town |
| Brookline town | 22 | 548 | 541 | 0.37% | 43 | 12.85 | Town |
| Saxtons River | 23 | 469 | 476 | -0.21% | 1,000 | 0.47 | Village |
| Windham town | 24 | 456 | 451 | 0.22% | 17 | 26.09 | Town |
| Stratton town | 25 | 447 | 442 | 0.22% | 10 | 46.03 | Town |
| Athens town | 26 | 398 | 395 | 0.25% | 29 | 13.95 | Town |
| Wilmington | 27 | 366 | 475 | -1.61% | 338 | 1.08 | CDP |
| Putney | 28 | 319 | 394 | -4.2% | 228 | 1.40 | CDP |
| Westminster | 29 | 289 | 286 | 0.35% | 212 | 1.36 | Village |
| Algiers | 30 | 282 | 170 | 6.82% | 434 | 0.65 | CDP |
| Harmonyville | 31 | 272 | 188 | 7.09% | 829 | 0.33 | CDP |
| South Londonderry | 32 | 268 | 291 | 7.2% | 431 | 0.62 | CDP |
| Jacksonville | 33 | 220 | 215 | 0.46% | 193 | 1.14 | Village |
| Townshend | 34 | 212 | 122 | 7.07% | 607 | 0.35 | CDP |
| North Westminster | 35 | 164 | 87 | 7.19% | 337 | 0.49 | CDP |
| Whitingham | 36 | 136 | 127 | 7.09% | 840 | 0.16 | CDP |
| Wardsboro | 37 | 123 | 89 | 7.89% | 1,108 | 0.11 | CDP |
| Grafton | 38 | 109 | 37 | 6.86% | 845 | 0.13 | CDP |
| Newfane | 39 | 92 | 92 | 0% | 523 | 0.18 | Village |
| Jamaica | 40 | 85 | 42 | 7.59% | 111 | 0.77 | CDP |
| Londonderry | 41 | 85 | 92 | 7.59% | 238 | 0.36 | CDP |
| West Dummerston | 42 | 71 | 44 | 7.58% | 550 | 0.13 | CDP |
Brattleboro town is the largest city in Windham County, with a population of 12,084.
West Dummerston is the smallest city in Windham County.
There are 42 cities in Windham County, Vermont.