Keswick Hall at Monticello
Where it is: Keswick, Virginia
What it Costs: $305
What You Get: There's no better base for exploring Virginia's award-winning wine country than this century-old 600-acre estate just five minutes from Monticello, where Thomas Jefferson experimented with grapevines. Anchored by the Villa Crawford, a 1912 Tuscan-style manse, Keswick presents a rare combination of elegance and warmth, along with a suitably old-world vibe: The 48 guest rooms are appointed with period antiques, many of which were chosen by former owner Bernard Ashley, the widower of country-chic design icon Laura Ashley. Among the many ways guests can enjoy the fruits of local vintners' labors: Book a private dinner for 2 to 12 guests in the stone-walled, 5,200-bottle cellar, devote half a day to a four-part vinotherapy spa treatment ($465), or attend monthly themed wine dinners ("Wines of Spain and Portugal" or "Celebrity Wine Makers"). The staff can also arrange tours of two dozen surrounding producers or help you draft a plan for making the most of Virginia Wine Month, happening now. keswick.com
Room to Book: Suite 9, with its original Georgia heart-pine floors, looks much as it did in 1912, when it was the first owner's master bedroom (from $525).
Priceless Perk: Watching the Keswick Hunt Club's bloodhounds trot alongside their master during their misty morning walk.
Luxe for Less: The Farmhouse at Veritas
Where it is: Afton, Virginia
What it Costs: $150
What You Get: Just booking one of the six refined guest rooms in this 1836 farmhouse in the Blue Ridge foothills guarantees you a complimentary bottle of Veritas wine—but a quick walk over to the winery itself (plus a $10 fee) will earn you a 30-minute tour and the chance to taste six vintages on the sunny porch. Weather permitting, four-course winemaker dinners with Veritas pairings are held in the just-built Garden House pavilion. veritasfarmhouse.com