| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density (/mi²) | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Bennington | 1 | 14,802 | 15,301 | -1.01% | 353 | 42 | Town |
| Manchester | 2 | 4,364 | 4,482 | -1.11% | 104 | 42 | Town |
| Shaftsbury | 3 | 3,528 | 3,594 | -0.84% | 82 | 43 | Town |
| Pownal | 4 | 3,190 | 3,264 | -0.9% | 68 | 47 | Town |
| Arlington | 5 | 2,381 | 2,457 | -0.96% | 57 | 42 | Town |
| Dorset | 6 | 2,096 | 2,138 | -0.8% | 44 | 47 | Town |
| North Bennington | 7 | 1,683 | 1,717 | -0.3% | 899 | 2 | Village |
| Winhall | 8 | 1,133 | 1,184 | -1.22% | 26 | 44 | Town |
| Sunderland | 9 | 1,055 | 1,056 | -0.28% | 23 | 45 | Town |
| Stamford | 10 | 838 | 863 | -1.18% | 21 | 39 | Town |
| Manchester | 11 | 755 | 772 | -0.26% | 214 | 4 | Village |
| Readsboro | 12 | 678 | 706 | -1.17% | 19 | 36 | Town |
| Rupert | 13 | 675 | 698 | -1.03% | 15 | 45 | Town |
| Peru | 14 | 521 | 529 | -0.38% | 14 | 37 | Town |
| Sandgate | 15 | 376 | 383 | -0.79% | 9.0 | 42 | Town |
| Woodford | 16 | 342 | 355 | -1.16% | 7.0 | 47 | Town |
| Landgrove | 17 | 167 | 174 | -1.76% | 19 | 9 | Town |
| Searsburg | 18 | 122 | 127 | -1.61% | 6.0 | 21 | Town |
| Old Bennington | 19 | 121 | 128 | -0.82% | 329 | 0 | Village |
Bennington is the largest city in Bennington County, with a population of 14,802.
Old Bennington is the smallest city in Bennington County, with a population of 121.
There are 19 cities in Bennington County, Vermont.