24 cities
| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Keene | 1 | 23,166 | 23,046 | 0.28% | 625 | 37 | City |
| Keene | 2 | 23,031 | 23,046 | -0.01% | 621 | 37 | City |
| Swanzey | 3 | 7,515 | 7,289 | 0.35% | 167 | 45 | Town |
| Rindge | 4 | 6,639 | 6,494 | 0.73% | 179 | 37 | Town |
| Jaffrey | 5 | 5,665 | 5,327 | 1.03% | 148 | 38 | Town |
| Winchester | 6 | 4,285 | 4,141 | 0.35% | 78 | 55 | Town |
| Hinsdale | 7 | 4,067 | 3,949 | 0.49% | 198 | 21 | Town |
| Walpole | 8 | 3,759 | 3,638 | 0.56% | 107 | 35 | Town |
| Chesterfield | 9 | 3,688 | 3,558 | 0.38% | 81 | 46 | Town |
| Fitzwilliam | 10 | 2,547 | 2,357 | 1.27% | 74 | 35 | Town |
| Marlborough | 11 | 2,245 | 2,098 | 1.17% | 110 | 20 | Town |
| Troy | 12 | 2,220 | 2,140 | 0.5% | 127 | 17 | Town |
| Alstead | 13 | 1,955 | 1,870 | 0.77% | 50 | 39 | Town |
| Westmoreland | 14 | 1,751 | 1,707 | 0.4% | 49 | 36 | Town |
| Dublin | 15 | 1,625 | 1,530 | 0.99% | 58 | 28 | Town |
| Stoddard | 16 | 1,485 | 1,383 | 1.23% | 29 | 51 | Town |
| Richmond | 17 | 1,255 | 1,197 | 0.64% | 33 | 38 | Town |
| Harrisville | 18 | 1,009 | 984 | 0.3% | 54 | 19 | Town |
| Surry | 19 | 875 | 821 | 0.81% | 56 | 16 | Town |
| Marlow | 20 | 800 | 747 | 1.65% | 31 | 26 | Town |
| Gilsum | 21 | 790 | 754 | 0.25% | 47 | 17 | Town |
| Sullivan | 22 | 719 | 658 | 1.7% | 39 | 19 | Town |
| Nelson | 23 | 685 | 632 | 1.33% | 31 | 22 | Town |
| Roxbury | 24 | 225 | 222 | 0% | 19 | 12 | Town |
Keene is the largest city in Cheshire County, with a population of 23,166.
Roxbury is the smallest city in Cheshire County, with a population of 225.
There are 24 cities in Cheshire County, New Hampshire.