1.Blowing In The 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, http://www.tidewater-vacations.com
2. Green Acres
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, http://www.tidewatervacations.com
3.Lounge Act
Please pass the margaritas—and the sunscreen! Bathing beauties will love the glamorous heated pool at Green Shadow Barn, a nearly one-hundred-year-old Royal Oak property. Converted into a 4,000-square-foot residence some fifty years ago, it’s crisply decorated with white walls and casual Pottery Barn-style furnishings. The four-bedroom’s contemporary-style pool overlooks the Tred Avon River and is landscaped with swaying native grasses and knockout roses. The surrounding stamped concrete patio, which brings the property’s 400 feet of shoreline into view, is the ideal place for a pool-side picnic. Stretch your (tan) legs and take a stroll down the 100-foot-long pier for a romantic view of Oxford, a stone’s thrown across the river.—K.B.
Price tag: $2,184-$5,509 per week
Book it: 410-770-9093, http://www.easternshore-vacations.com
4.Sweet Dreams
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, http://www.tidewatervacations.com
5. A Slice Of Heaven
When he first saw Heavenly Haven, the owner of a high-end restaurant chain found its layout so heavenly—but not its décor—that he footed the bill for a complete interior makeover. While he only visits five months out of the year, you—and twelve friends—can benefit from his investment. Basically three houses in one, the 4,500-square-foot Colonial mansion incorporates three kitchens, six bedrooms (each with en suite bath), two laundry rooms, pool, playground, and two-bedroom guest cottage. The piece de resistance? A 1,900-square-foot kitchen/dining room/ living room area, where the entire crew can eat—or play a set of tennis.—K.B.
Price tag: $2,974-$7,629 per week
Book it: 410-770-9093, http://www.easternshorevacations.com
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 Mediterranean.—J.S.
Price tag: $8,000 per week
Book it: 410-745-5255, http://www.tidewater-vacations.com
7.Docking Station
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, http://www.tidewatervacations.com
8.To The Manor Born
The first brick house constructed in Talbot County, Hampden is the sort of place Brideshead Revisited’s Lady Marchmain would rent—if she vacationed in Trappe. The 1663 ninety-acre estate on La Trappe Creek is an Anglophile’s paradise, complete with oil portraiture, leather couches, Oriental rugs, and antiques. Apropos of the landed gentry theme, horseback riding is available via the on-site stables, which house five horses, and hunting is permitted on the property. Lords and ladies will appreciate the posh master bedroom suite, with French doors that open to the creek,marble-floored bathroom, walk-in closets, and fireplace. With five bedrooms (each with private bath) in the main house and a three-bedroom guest cottage, there’s ample space for twenty of your nearest and dearest.—K.B.
Price tag: $2,571-$6,228 per week
Book it: 410-770-9093, http://www.easternshorevacations.com
9.Chef’s Choice
Bet the Barefoot Contessa wouldn’t mind padding around this kitchen. Sited on five acres on Peach Blossom Creek, Blue Gates is a chef’s dream house, complete with Wolf cooking range, granite countertops, Sub-Zero fridge, and hand-pounded copper sink with matching fixtures. If you prefer to pass on cooking, Easton’s fabulous restaurants are only minutes away. “What people like about this house is that you feel as though you’re on a French country estate but you’re only two minutes from town,” says Eastern Shore Vacation Rentals co-owner Betsy Greaney. Decorated in soft blues, greens, and yellows, the house sleeps eight and includes a swimming pool and deep-water dock. And keep your eyes peeled for this house on the silver screen: A host of Hollywood producers recently scouted it for an upcoming movie.—K.B.
Price tag: $4,552-$7,052 per week
Book it: 410-770-9093, http://www.easternshorevacations.com
