32 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Keene city | 1 | 22,893 | 23,051 | -0.05% | 617 | 37.09 | City |
| Keene | 2 | 22,827 | 23,051 | -0.2% | 615 | 37.09 | City |
| Swanzey town | 3 | 7,432 | 7,281 | 0.03% | 165 | 44.98 | Town |
| Rindge town | 4 | 6,795 | 6,492 | 1.49% | 183 | 37.11 | Town |
| Jaffrey town | 5 | 5,553 | 5,331 | 0.45% | 145 | 38.40 | Town |
| Winchester town | 6 | 4,268 | 4,148 | 0.21% | 78 | 54.99 | Town |
| Hinsdale town | 7 | 3,998 | 3,951 | -0.1% | 195 | 20.52 | Town |
| Walpole town | 8 | 3,692 | 3,637 | -0.05% | 105 | 35.23 | Town |
| Chesterfield town | 9 | 3,685 | 3,558 | 0.46% | 81 | 45.56 | Town |
| Jaffrey | 10 | 3,106 | 2,750 | 0.78% | 912 | 3.40 | CDP |
| Fitzwilliam town | 11 | 2,478 | 2,357 | 0.57% | 72 | 34.63 | Town |
| Troy town | 12 | 2,202 | 2,140 | 0.27% | 126 | 17.46 | Town |
| Marlborough town | 13 | 2,201 | 2,096 | 0.73% | 108 | 20.41 | Town |
| Alstead town | 14 | 1,926 | 1,868 | 0.36% | 50 | 38.83 | Town |
| Westmoreland town | 15 | 1,742 | 1,708 | 0.29% | 49 | 35.81 | Town |
| Dublin town | 16 | 1,594 | 1,534 | 0.44% | 57 | 27.89 | Town |
| Stoddard town | 17 | 1,461 | 1,382 | 1.04% | 29 | 50.93 | Town |
| Hinsdale | 18 | 1,403 | 1,470 | -0.71% | 604 | 2.32 | CDP |
| Winchester | 19 | 1,278 | 1,939 | -2.29% | 429 | 2.98 | CDP |
| Richmond town | 20 | 1,245 | 1,197 | 0.65% | 33 | 37.54 | Town |
| West Swanzey | 21 | 1,173 | 1,180 | -0.76% | 455 | 2.58 | CDP |
| Harrisville town | 22 | 1,002 | 984 | 0% | 54 | 18.65 | Town |
| Marlborough | 23 | 965 | 1,093 | -0.92% | 572 | 1.69 | CDP |
| Surry town | 24 | 856 | 821 | 0.12% | 55 | 15.69 | Town |
| Troy | 25 | 845 | 857 | -2.87% | 662 | 1.28 | CDP |
| Gilsum town | 26 | 802 | 755 | 1.01% | 48 | 16.67 | Town |
| Marlow town | 27 | 755 | 747 | -0.26% | 29 | 25.97 | Town |
| Sullivan town | 28 | 702 | 657 | 1.45% | 38 | 18.54 | Town |
| Nelson town | 29 | 679 | 633 | 1.49% | 31 | 21.91 | Town |
| North Walpole | 30 | 490 | 560 | -4.48% | 706 | 0.69 | CDP |
| Walpole | 31 | 430 | 647 | -2.71% | 353 | 1.22 | CDP |
| Roxbury town | 32 | 222 | 219 | 0% | 19 | 11.91 | Town |
Keene city is the largest city in Cheshire County, with a population of 22,893.
Roxbury town is the smallest city in Cheshire County.
There are 32 cities in Cheshire County, New Hampshire.