27 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Brattleboro | 1 | 11,841 | 12,167 | -1.12% | 369 | 32 | Town |
| Rockingham | 2 | 4,692 | 4,836 | -1.12% | 113 | 41 | Town |
| Westminster | 3 | 2,952 | 3,003 | -0.94% | 66 | 45 | Town |
| Bellows Falls | 4 | 2,727 | 2,789 | -0.47% | 2,007 | 1 | Village |
| Putney | 5 | 2,582 | 2,616 | -0.58% | 97 | 27 | Town |
| Wilmington | 6 | 2,311 | 2,250 | 0.83% | 57 | 40 | Town |
| Vernon | 7 | 2,150 | 2,181 | -1.06% | 111 | 19 | Town |
| Guilford | 8 | 2,085 | 2,122 | -1.04% | 53 | 40 | Town |
| Londonderry | 9 | 1,912 | 1,918 | -0.57% | 54 | 35 | Town |
| Dummerston | 10 | 1,848 | 1,863 | -0.86% | 60 | 31 | Town |
| Dover | 11 | 1,830 | 1,801 | -0.27% | 51 | 36 | Town |
| Marlboro | 12 | 1,776 | 1,727 | 0.23% | 44 | 40 | Town |
| Newfane | 13 | 1,640 | 1,645 | -0.55% | 41 | 40 | Town |
| Whitingham | 14 | 1,347 | 1,339 | -0.3% | 37 | 37 | Town |
| Townshend | 15 | 1,269 | 1,288 | -1.01% | 30 | 42 | Town |
| Jamaica | 16 | 977 | 998 | -1.21% | 20 | 49 | Town |
| Wardsboro | 17 | 853 | 868 | -0.93% | 29 | 29 | Town |
| Halifax | 18 | 750 | 777 | -1.32% | 19 | 40 | Town |
| Grafton | 19 | 630 | 644 | -1.25% | 17 | 38 | Town |
| Brookline | 20 | 533 | 542 | -1.11% | 41 | 13 | Town |
| Saxtons River | 21 | 464 | 476 | -0.64% | 989 | 0 | Village |
| Windham | 22 | 460 | 452 | 0.66% | 18 | 26 | Town |
| Stratton | 23 | 442 | 443 | -0.45% | 10 | 46 | Town |
| Athens | 24 | 385 | 394 | -1.28% | 28 | 14 | Town |
| Westminster | 25 | 284 | 286 | -0.35% | 208 | 1 | Village |
| Jacksonville | 26 | 219 | 214 | 0.46% | 192 | 1 | Village |
| Newfane | 27 | 94 | 93 | 0% | 534 | 0 | Village |
Brattleboro is the largest city in Windham County, with a population of 11,841.
Newfane is the smallest city in Windham County, with a population of 94.
There are 27 cities in Windham County, Vermont.