Laps of Luxury

Can’t afford that multimillion-dollar Talbot County dream house? At these nine palatial estates, you can live the good life for a week at a time.

  1.  Blowing In The Wind

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay, Prarie Wind
If your tastes tend toward contemporary, there are few more stunning homes on the Bay than Prairie Wind, located just outside of St. Michaels. Designed by Washington architect Suman Sorg and Associates and landscaped by fellow D.C.’er James van Sweden, Prairie Wind looks like a home straight out of last’s month’s Architectural Digest. Three attached wooden buildings house a central living area with funky modern furnishings—chairs and loveseats come in vibrant reds, yellows, and oranges. Views out of the two-story, floor-to-ceiling windows are of tall reed grass and sunsets over the Bay. (Heck, even the view from the bathtub is stunning.) The adjacent buildings house two master bedrooms and full baths. If you can ever tear yourself away, a circular swimming pool surrounded by more reed grass awaits outside, as do several footpaths leading down to a private Bay-side beach.—J.S.

Price tag: $5,000 per week

Book it: 410-745-5255

2.  Green Acres

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay, Millwood Manor.
Ah, the pleasures of estate life: just you, the wildlife, and a host of groundsmen, all of whom are charged with maintaining Millwood Manor’s 100 acres. Take a jog along the miles of mowed paths, most of which border the Tred Avon River or stop and smell the roses blooming in the six-acre garden. The three-bedroom, circa-1800 property—complete with a two-bedroom guest cottage, tennis court, and resident pheasants—was occupied by Owen Wilson while filming Wedding Crashers. But it’s anything but high-profile thanks to its mile-and-a-half, tree-lined driveway that keeps the estate wonderfully hidden from the rest of the world.—K.B.

Price tag: $8,000-$10,000 per week

Book it: 410-745-5255

4.  Sweet Dreams

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay, Sycamore Llanding.
Chandeliers, chaises, and 600-thread-count cotton sheets. What more can you ask for in a master bedroom—except, of course, a fireplace, four-poster king-size bed, and plush carpet? Sycamore Landing has these spoiling details—and more. Modern-day princesses (and princes) will also appreciate the suite’s walk-in closet, and great view of the Miles River. The circa-1659, five-bedroom property is one of the oldest estates in the county and is a favorite haunt among Washington, D.C., politicos, who likely prefer the library, complete with grand piano and deep leather sofas. Brandy and cigars before retiring, anyone?—K.B.

Price tag: $5,000-$7,000 per week

Book it: 410-745-5255

6.Thomas Jefferson (Would’ve) Slept Here

If you’ve ever wanted to stay the night at Thomas Jefferson’s Monticello—but the guards kicked you out at closing time—then book San Sano, located between Easton and St. Michaels. The regal, multicolumned entryway clearly shows T.J.’s influence, and pulling up along the white gravel lane lined with London plane trees and loblolly pines gives guests a reception worthy of a president. (Or someone with pockets just as deep.) The cream and beige five-bedroom interior is decidedly more modern and accented with stone—the enormous dining room marble fireplace looks as if it could burn a sequoia. Spend your days exploring the 146-acre grounds, five of which accommodate a vineyard, which supplies grapes to Little Ashby Winery nearby. The estate’s name is a nod to a small Italian town, and if you try hard enough while sipping Campari and soda by the home’s enormous swimming pool, you just might convince yourself that those Bay breezes are really


Price tag: $8,000 per week

Book it: 410-745-5255

7.Docking Station

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay | Kirkland Manor
You can pull your Bay cruiser right up to the deep-water dock at Kirkland Hall Manor, a sprawling 1920s, white-pillared Georgian estate, located outside of St. Michaels. Unload your baggage at the private boat house and then stroll across the broad lawn (pass by the swimming pool) to the estate, where the nautical décor theme continues. Inside, there are six bedrooms—five of which have their own private baths and sitting rooms—and a dining room table long enough to accommodate nearly everyone on board. If the weather is iffy, relax with a hardback in the library, tickle the ivories on the baby grand piano, or retire to the game room for a gentlemanly poker match.—J.S.

Price tag: $12,000 per week

Book it: 410-745-5255