19 cities
| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Bennington | 1 | 14,969 | 15,306 | -0.51% | 357 | 42 | Town |
| Manchester | 2 | 4,424 | 4,480 | -0.43% | 105 | 42 | Town |
| Shaftsbury | 3 | 3,557 | 3,595 | -0.5% | 83 | 43 | Town |
| Pownal | 4 | 3,240 | 3,264 | -0.28% | 69 | 47 | Town |
| Arlington | 5 | 2,422 | 2,458 | -0.25% | 58 | 42 | Town |
| Dorset | 6 | 2,140 | 2,136 | 0% | 45 | 47 | Town |
| North Bennington | 7 | 1,692 | 1,718 | -0.24% | 903 | 2 | Village |
| Winhall | 8 | 1,148 | 1,184 | -0.69% | 26 | 44 | Town |
| Sunderland | 9 | 1,074 | 1,055 | 0.66% | 24 | 45 | Town |
| Stamford | 10 | 851 | 862 | -0.47% | 22 | 39 | Town |
| Manchester | 11 | 764 | 772 | -0.13% | 216 | 4 | Village |
| Readsboro | 12 | 686 | 705 | -0.72% | 19 | 36 | Town |
| Rupert | 13 | 685 | 697 | -0.44% | 15 | 45 | Town |
| Peru | 14 | 524 | 528 | -0.19% | 14 | 37 | Town |
| Sandgate | 15 | 380 | 382 | -0.26% | 9 | 42 | Town |
| Woodford | 16 | 345 | 355 | -0.58% | 7 | 47 | Town |
| Landgrove | 17 | 172 | 173 | 0% | 19 | 9 | Town |
| Old Bennington | 18 | 131 | 134 | 0% | 356 | 0 | Village |
| Searsburg | 19 | 123 | 125 | -0.81% | 6 | 21 | Town |
Bennington is the largest city in Bennington County, with a population of 14,969.
Searsburg is the smallest city in Bennington County, with a population of 123.
There are 19 cities in Bennington County, Vermont.