Where to stay: While you could drive back to D.C., you'll save by staying local. According to research firm STR, the average hotel in Middleburg's Loudoun County is 66% cheaper than lodging in the capital.
The Middleburg Country Inn (from $105 weekdays and $120 weekends) has rooms decorated with period Southern charm and one of the best complimentary breakfasts in town, says Jackie Brown-Saunders with Visit Loudoun.
For a bit more, you could also opt for one of the eight Easter-egg-colored rooms (or the freestanding cottage) at the Briar Patch B&B, where fall rates start at $150.
Take a vineyard break: Stroll down Middleburg's main drag, Washington Street. In shop David Ladd & Co., you'll find handsome highball and gimlet glasses decorated with the town's unofficial mascot, a very posh fox. Drive to Upperville, a few miles away, to the Hunter's Head Tavern, suggests Loudoun Times-Mirror reporter Trevor Baratko. If it's warm enough, snag a table in the stone courtyard (lunch, $20).