| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Brattleboro | 1 | 11,814 | 12,163 | -0.49% | 369 | 32 | Town |
| Rockingham | 2 | 4,647 | 4,846 | -1.06% | 112 | 41 | Town |
| Westminster | 3 | 2,908 | 2,984 | -0.82% | 65 | 45 | Town |
| Bellows Falls | 4 | 2,691 | 2,794 | -0.55% | 1,980 | 1 | Village |
| Putney | 5 | 2,563 | 2,615 | -0.47% | 96 | 27 | Town |
| Wilmington | 6 | 2,276 | 2,250 | -0.18% | 56 | 40 | Town |
| Vernon | 7 | 2,123 | 2,180 | -0.98% | 109 | 19 | Town |
| Guilford | 8 | 2,059 | 2,124 | -1.1% | 52 | 40 | Town |
| Londonderry | 9 | 1,886 | 1,912 | -0.58% | 53 | 35 | Town |
| Dummerston | 10 | 1,850 | 1,870 | -0.48% | 60 | 31 | Town |
| Dover | 11 | 1,826 | 1,799 | -0.05% | 51 | 36 | Town |
| Marlboro | 12 | 1,787 | 1,724 | 0.62% | 44 | 40 | Town |
| Newfane | 13 | 1,626 | 1,646 | -0.61% | 41 | 40 | Town |
| Whitingham | 14 | 1,325 | 1,341 | -0.82% | 36 | 37 | Town |
| Townshend | 15 | 1,246 | 1,283 | -1.03% | 29 | 42 | Town |
| Jamaica | 16 | 968 | 1,000 | -1.12% | 20 | 49 | Town |
| Wardsboro | 17 | 847 | 870 | -0.82% | 29 | 29 | Town |
| Halifax | 18 | 741 | 776 | -1.07% | 19 | 40 | Town |
| Grafton | 19 | 627 | 642 | -0.63% | 16 | 38 | Town |
| Brookline | 20 | 525 | 542 | -1.13% | 41 | 13 | Town |
| Saxtons River | 21 | 461 | 479 | -0.65% | 983 | 0 | Village |
| Windham | 22 | 457 | 450 | 0.44% | 18 | 26 | Town |
| Stratton | 23 | 439 | 442 | -0.23% | 10 | 46 | Town |
| Athens | 24 | 385 | 395 | -1.03% | 28 | 14 | Town |
| Westminster | 25 | 276 | 282 | -0.36% | 202 | 1 | Village |
| Jacksonville | 26 | 214 | 215 | 0% | 188 | 1 | Village |
| Newfane | 27 | 91 | 93 | -1.09% | 517 | 0 | Village |
Brattleboro is the largest city in Windham County, with a population of 11,814.
Newfane is the smallest city in Windham County, with a population of 91.
There are 27 cities in Windham County, Vermont.