Looking for an Eastern Shore waterfront retreat that's perfect for a romantic long weekend, a family vacation with the kids, or just a place for you to rejuvenate? Welcome to ''Overlook on Dun's Cove!'' Relax in this custom-built vacation home in an exceptionally private wooded lot of almost 3 acres, yet minutes from fine dining, eateries, museums, and shops in St. Michaels, Easton and Tilghman. This idyllic property boasts glorious views, abundant wildfowl, and its own deep water pier which accommodates sail or power yachts up to 40 feet - also great for crabbing and fishing! (Adults and kids alike note their productive catches in our Guest Book. Two crab pots are available on-site for guests.) The pier is equipped with shore power, water, lights, and a dock storage box. Steps at the other end of the bulkhead provide a convenient launch for kayaks and paddle boards.

Recent upgrades assure luxury, comfort, and functionality that will delight the most discerning vacation rental guests. The living and dining areas, master bedroom, and home office/den have premium red oak hardwood floors. Stylish wool rugs define different areas in the open concept living space. The master bedroom has a Queen bed in a handsome iron frame with an aged pewter finish.

Whether you are an enthusiastic chef or prefer the convenience of takeout, you will enjoy using the gourmet kitchen. Its premier appliances include a SubZero refrigerator, Jenn-Aire range and microwave, and an Asko dishwasher. Inside the driftwood gray all-wood kitchen cabinets and drawers, you will find chef-quality cookware, bakeware, and utensils including All-Clad stainless pots, non-stick fry pans and a sauté pan, J.A. Henckels knives, Le Creuset Dutch oven and cast iron fry pan, and a stockpot for crabs and lobsters. The upper cabinets between the kitchen and dining area have glass inserts where you can readily access the Apilco French porcelain “Tradition” dinnerware plus a full complement of glassware (red wine, white wine, short (old fashioned), martini and tall (iced tea/soda/beer) glasses, champagne flutes, and juice tumblers) on the shelves.

Each of the two bedrooms has its own full bathroom with marble floor and an undermount porcelain sink set in a Misty Carrera quartz vanity top. These bathrooms feature high-end polished chrome fixtures; glossy white subway tile; new alcove soaker tub, shower, and toilet (master bathroom); new tile walk-in shower (upstairs bathroom); and custom frameless glass shower enclosures (both bathrooms).

The home has a soft contemporary interior décor. Furnishings and amenities include HDTV with Netflix, DVD player, Bose CD/radio; modern home office with high-speed (250 Mbps) WiFi and cable internet access and a laser printer; Saber outdoor stainless gas grill, and all-weather patio furniture. Other notable features are Carrier heat pump and central air conditioning with individually controlled thermostat; Asko high efficiency washer and dryer; wood-burning fireplace (with ample supply of firewood); wrap-around deck that’s great for entertaining; professional mosquito and insect control protection for comfort outdoors; weekly housecleaning and linen changeout at no extra charge for rentals of two weeks or longer; and hand-ironed sheets and luxurious fluffy towels.

Available year-round for weekend, weekly, or longer rentals. NOTE: A 4-night minimum is normally required for rentals during the busiest prime season, May 15 - October 15. Talbot County Law requires at least a 3-night minimum throughout the year.

Weekly rates are discounted 11% to 12% off nightly rates. Nightly rates are: $280 for January 5, 2026 - February 28, 2026; $300 for March 1 - May 14, 2026; $340 for May 15 - October 15, 2026 (peak season); $300 for October 16 - December 18, 2026; and $315 for December 19, 2026 - January 3, 2027.

The following accolade in our Guest Book reflects the exquisite vacation rental experience at Overlook on Dun’s Cove: “This home is gentle and kind; it’s a real Chesapeake Bay treasure. Our heartfelt thanks for creating such a gracious haven to rest and replenish.”


--Talbot County Short-Term Rental License: STRN-24-56.