32 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Bennington | 1 | 15,045 | 15,306 | -0.5% | 359 | 42 | Town |
| Bennington | 2 | 8,673 | 8,539 | -0.31% | 1,796 | 5 | CDP |
| Manchester | 3 | 4,443 | 4,480 | -0.43% | 106 | 42 | Town |
| Shaftsbury | 4 | 3,575 | 3,595 | -0.5% | 83 | 43 | Town |
| Pownal | 5 | 3,249 | 3,264 | -0.28% | 69 | 47 | Town |
| Arlington | 6 | 2,428 | 2,458 | -0.25% | 58 | 42 | Town |
| Dorset | 7 | 2,140 | 2,136 | 0% | 45 | 47 | Town |
| Arlington | 8 | 1,923 | 1,483 | 2.51% | 501 | 4 | CDP |
| Manchester Center | 9 | 1,764 | 2,272 | -1.34% | 381 | 5 | CDP |
| North Bennington | 10 | 1,696 | 1,718 | -0.29% | 905 | 2 | Village |
| Winhall | 11 | 1,156 | 1,184 | -0.69% | 26 | 44 | Town |
| Sunderland | 12 | 1,067 | 1,055 | 0.66% | 24 | 45 | Town |
| Stamford | 13 | 855 | 862 | -0.47% | 22 | 39 | Town |
| Manchester | 14 | 765 | 772 | -0.26% | 216 | 4 | Village |
| Pownal | 15 | 695 | 666 | 7.09% | 1,355 | 1 | CDP |
| Readsboro | 16 | 691 | 705 | -0.72% | 19 | 36 | Town |
| Rupert | 17 | 688 | 697 | -0.43% | 15 | 45 | Town |
| Stamford | 18 | 666 | 465 | 7.07% | 124 | 5 | CDP |
| Pownal Center | 19 | 649 | 614 | 7.1% | 417 | 2 | CDP |
| Peru | 20 | 525 | 528 | -0.19% | 14 | 37 | Town |
| North Pownal | 21 | 488 | 478 | 7.25% | 410 | 1 | CDP |
| Dorset | 22 | 405 | 387 | 2.53% | 195 | 2 | CDP |
| Sandgate | 23 | 381 | 382 | -0.26% | 9 | 42 | Town |
| South Shaftsbury | 24 | 363 | 459 | -5.47% | 162 | 2 | CDP |
| Woodford | 25 | 347 | 355 | -0.57% | 7 | 47 | Town |
| East Dorset | 26 | 316 | 205 | 7.12% | 142 | 2 | CDP |
| Readsboro | 27 | 275 | 309 | -1.08% | 224 | 1 | CDP |
| Landgrove | 28 | 172 | 173 | 0% | 19 | 9 | Town |
| Old Bennington | 29 | 131 | 134 | -0.76% | 356 | 0 | Village |
| Searsburg | 30 | 124 | 125 | -0.8% | 6 | 21 | Town |
| Stratton Mountain | 31 | 71 | 29 | 7.58% | 27 | 3 | CDP |
| Chimney Hill | 32 | 47 | 23 | 6.82% | 23 | 2 | CDP |
Bennington is the largest city in Bennington County, with a population of 15,045.
Chimney Hill is the smallest city in Bennington County, with a population of 47.
There are 32 cities in Bennington County, Vermont.