32 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Bennington town | 1 | 15,014 | 15,307 | -0.62% | 358 | 41.95 | Town |
| Bennington | 2 | 8,673 | 8,539 | -0.31% | 1,796 | 4.83 | CDP |
| Manchester town | 3 | 4,457 | 4,477 | -0.27% | 106 | 41.95 | Town |
| Shaftsbury town | 4 | 3,616 | 3,594 | 0.08% | 84 | 42.99 | Town |
| Pownal town | 5 | 3,242 | 3,258 | -0.28% | 69 | 46.77 | Town |
| Arlington town | 6 | 2,410 | 2,458 | -0.66% | 57 | 42.03 | Town |
| Dorset town | 7 | 2,125 | 2,135 | -0.33% | 45 | 47.37 | Town |
| Arlington | 8 | 1,923 | 1,483 | 2.51% | 501 | 3.83 | CDP |
| Manchester Center | 9 | 1,764 | 2,272 | -1.34% | 381 | 4.63 | CDP |
| North Bennington | 10 | 1,699 | 1,714 | -0.18% | 907 | 1.87 | Village |
| Winhall town | 11 | 1,158 | 1,184 | -0.6% | 26 | 44.05 | Town |
| Sunderland town | 12 | 1,048 | 1,056 | -0.38% | 23 | 45.23 | Town |
| Stamford town | 13 | 861 | 862 | -0.23% | 22 | 39.48 | Town |
| Manchester | 14 | 771 | 771 | 0% | 218 | 3.54 | Village |
| Pownal | 15 | 695 | 666 | 7.09% | 1,355 | 0.51 | CDP |
| Readsboro town | 16 | 691 | 703 | -0.58% | 19 | 36.13 | Town |
| Rupert town | 17 | 687 | 696 | -0.43% | 15 | 44.75 | Town |
| Stamford | 18 | 666 | 465 | 7.07% | 124 | 5.36 | CDP |
| Pownal Center | 19 | 649 | 614 | 7.1% | 417 | 1.56 | CDP |
| Peru town | 20 | 526 | 527 | 0% | 14 | 37.37 | Town |
| North Pownal | 21 | 488 | 478 | 7.25% | 410 | 1.19 | CDP |
| Dorset | 22 | 405 | 387 | 2.53% | 195 | 2.08 | CDP |
| Sandgate town | 23 | 381 | 382 | -0.26% | 9 | 42.25 | Town |
| South Shaftsbury | 24 | 363 | 459 | -5.47% | 162 | 2.24 | CDP |
| Woodford town | 25 | 344 | 354 | -0.86% | 7 | 47.36 | Town |
| East Dorset | 26 | 316 | 205 | 7.12% | 142 | 2.22 | CDP |
| Readsboro | 27 | 275 | 309 | -1.08% | 224 | 1.23 | CDP |
| Landgrove town | 28 | 172 | 175 | -0.58% | 19 | 8.86 | Town |
| Old Bennington | 29 | 130 | 134 | -0.76% | 353 | 0.37 | Village |
| Searsburg town | 30 | 124 | 126 | -0.8% | 6 | 21.28 | Town |
| Stratton Mountain | 31 | 71 | 29 | 7.58% | 27 | 2.63 | CDP |
| Chimney Hill | 32 | 47 | 23 | 6.82% | 23 | 2.07 | CDP |
Bennington town is the largest city in Bennington County, with a population of 15,014.
Chimney Hill is the smallest city in Bennington County.
There are 32 cities in Bennington County, Vermont.