5 cities
| City | Rank | County | 2025 Pop. ↓ |
|---|---|---|---|
| Rutland | 1 | Rutland County | 15,526 |
| North Bennington | 2 | Bennington County | 1,699 |
| Poultney | 3 | Rutland County | 1,100 |
| Manchester | 4 | Bennington County | 771 |
| Old Bennington | 5 | Bennington County | 130 |
Rutland County and Bennington County are the counties that are generally considered part of Southwest Vermont.