24 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Keene | 1 | 23,101 | 23,046 | 0.28% | 623 | 37 | City |
| Keene | 2 | 23,033 | 23,046 | -0.01% | 621 | 37 | City |
| Swanzey | 3 | 7,489 | 7,289 | 0.35% | 167 | 45 | Town |
| Rindge | 4 | 6,591 | 6,494 | 0.73% | 178 | 37 | Town |
| Jaffrey | 5 | 5,607 | 5,327 | 1.05% | 146 | 38 | Town |
| Winchester | 6 | 4,270 | 4,141 | 0.35% | 78 | 55 | Town |
| Hinsdale | 7 | 4,047 | 3,949 | 0.5% | 197 | 21 | Town |
| Walpole | 8 | 3,738 | 3,638 | 0.56% | 106 | 35 | Town |
| Chesterfield | 9 | 3,674 | 3,558 | 0.38% | 81 | 46 | Town |
| Fitzwilliam | 10 | 2,515 | 2,357 | 1.29% | 73 | 35 | Town |
| Marlborough | 11 | 2,219 | 2,098 | 1.19% | 109 | 20 | Town |
| Troy | 12 | 2,209 | 2,140 | 0.5% | 127 | 17 | Town |
| Alstead | 13 | 1,940 | 1,870 | 0.78% | 50 | 39 | Town |
| Westmoreland | 14 | 1,744 | 1,707 | 0.4% | 49 | 36 | Town |
| Dublin | 15 | 1,609 | 1,530 | 1% | 58 | 28 | Town |
| Stoddard | 16 | 1,467 | 1,383 | 1.24% | 29 | 51 | Town |
| Richmond | 17 | 1,247 | 1,197 | 0.65% | 33 | 38 | Town |
| Harrisville | 18 | 1,006 | 984 | 0.3% | 54 | 19 | Town |
| Surry | 19 | 868 | 821 | 0.81% | 55 | 16 | Town |
| Gilsum | 20 | 788 | 754 | 0.25% | 47 | 17 | Town |
| Marlow | 21 | 787 | 747 | 1.68% | 30 | 26 | Town |
| Sullivan | 22 | 707 | 658 | 1.73% | 38 | 19 | Town |
| Nelson | 23 | 676 | 632 | 1.35% | 31 | 22 | Town |
| Roxbury | 24 | 225 | 222 | 0% | 19 | 12 | Town |
Keene is the largest city in Cheshire County, with a population of 23,101.
Roxbury is the smallest city in Cheshire County, with a population of 225.
There are 24 cities in Cheshire County, New Hampshire.