| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Keene | 1 | 23,025 | 23,049 | -0.2% | 621 | 37 | City |
| Swanzey | 2 | 7,451 | 7,292 | -0.13% | 166 | 45 | Town |
| Rindge | 3 | 6,517 | 6,491 | 0.23% | 176 | 37 | Town |
| Jaffrey | 4 | 5,671 | 5,334 | 0.67% | 148 | 38 | Town |
| Winchester | 5 | 4,292 | 4,139 | 0.26% | 78 | 55 | Town |
| Hinsdale | 6 | 4,034 | 3,953 | 0% | 197 | 21 | Town |
| Chesterfield | 7 | 3,705 | 3,558 | 0.57% | 81 | 46 | Town |
| Walpole | 8 | 3,699 | 3,639 | -0.19% | 105 | 35 | Town |
| Fitzwilliam | 9 | 2,514 | 2,362 | 0.56% | 73 | 35 | Town |
| Marlborough | 10 | 2,218 | 2,092 | 0.77% | 109 | 20 | Town |
| Troy | 11 | 2,199 | 2,138 | 0.05% | 126 | 17 | Town |
| Alstead | 12 | 1,934 | 1,868 | 0.31% | 50 | 39 | Town |
| Westmoreland | 13 | 1,769 | 1,709 | 0.68% | 49 | 36 | Town |
| Dublin | 14 | 1,622 | 1,528 | 1.06% | 58 | 28 | Town |
| Stoddard | 15 | 1,483 | 1,386 | 1.02% | 29 | 51 | Town |
| Richmond | 16 | 1,231 | 1,195 | -0.24% | 33 | 38 | Town |
| Harrisville | 17 | 998 | 986 | -0.2% | 54 | 19 | Town |
| Surry | 18 | 860 | 822 | -0.23% | 55 | 16 | Town |
| Gilsum | 19 | 799 | 753 | 0.88% | 48 | 17 | Town |
| Marlow | 20 | 774 | 743 | 0.13% | 30 | 26 | Town |
| Sullivan | 21 | 697 | 658 | 0% | 38 | 19 | Town |
| Nelson | 22 | 659 | 628 | -0.3% | 30 | 22 | Town |
| Roxbury | 23 | 219 | 218 | -0.45% | 18 | 12 | Town |
Keene is the largest city in Cheshire County, with a population of 23,025.
Roxbury is the smallest city in Cheshire County, with a population of 219.
There are 23 cities in Cheshire County, New Hampshire.