11 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Bennington | 1 | 15,014 | 15,307 | -0.62% | 358 | 41.95 | Town |
| Manchester | 2 | 4,457 | 4,477 | -0.27% | 106 | 41.95 | Town |
| Shaftsbury | 3 | 3,616 | 3,594 | 0.08% | 84 | 42.99 | Town |
| Pownal | 4 | 3,242 | 3,258 | -0.28% | 69 | 46.77 | Town |
| Arlington | 5 | 2,410 | 2,458 | -0.66% | 57 | 42.03 | Town |
| Dorset | 6 | 2,125 | 2,135 | -0.33% | 45 | 47.37 | Town |
| North Bennington | 7 | 1,699 | 1,714 | -0.18% | 907 | 1.87 | Village |
| Winhall | 8 | 1,158 | 1,184 | -0.6% | 26 | 44.05 | Town |
| Sunderland | 9 | 1,048 | 1,056 | -0.38% | 23 | 45.23 | Town |
| Manchester | 10 | 771 | 771 | 0% | 218 | 3.54 | Village |
| Old Bennington | 11 | 130 | 134 | -0.76% | 353 | 0.37 | Village |
Bennington is the largest city in Bennington County, with a population of 15,014.
Old Bennington is the smallest city in Bennington County.
There are 11 cities in Bennington County, Vermont.