Entire home
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Riverside holiday home with kitchen and patio
Photo gallery for Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels





Reviews
10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4132.4 sq m
Popular amenities
Explore the area

Sherwood, MD
- Place, Knapp's Narrows Marina & Inn3 min drive
- Place, Back Creek Community Park3 min drive
- Place, Tilghman Island Marina4 min drive
- Airport, Easton, MD (ESN-Easton - Newnam)43 min drive
Rooms & beds
2 bedrooms (sleeps 4)
Master
1 Queen Bed
Upstairs Bedroom
2 Single Beds
2 bathrooms
Bathroom 1
Bathtub or shower · Bathtub · Toilet
Bathroom 2
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Office
Garden
Dining area
About this property
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
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 February 1 - 28, 2025; $295 for March 1 - May 14, 2025; $330 for May 15 - October 15, 2025 (peak season); $295 for October 16, 2025 - December 19, 2025; $315 for December 20, 2025 - January 4, 2026; $280 for January 5, 2026 - February 28, 2026; $295 for March 1 - May 14, 2026; $330 for May 15 - October 15, 2026 (peak season); $295 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.
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 February 1 - 28, 2025; $295 for March 1 - May 14, 2025; $330 for May 15 - October 15, 2025 (peak season); $295 for October 16, 2025 - December 19, 2025; $315 for December 20, 2025 - January 4, 2026; $280 for January 5, 2026 - February 28, 2026; $295 for March 1 - May 14, 2026; $330 for May 15 - October 15, 2026 (peak season); $295 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.
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Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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House Rules
Check in after 4:00 PM
Minimum age to rent: 22
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
Property Registration Number STRN-24-56
We should mention
A car is required for transport to and from this property
About the area
Sherwood
Located in Sherwood, this holiday home is in a rural area and on the waterfront. Back Creek Community Park and Kronsberg Park reflect the area's natural beauty and area attractions include Phillips Wharf Environmental Center and Chesapeake Bay Maritime Museum. Chesapeake Beach Railway Museum and Chesapeake Beach Water Park are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Sherwood, MD
What's nearby
- Knapp's Narrows Marina & Inn - 3 min drive - 2.8 km
- Back Creek Community Park - 3 min drive - 2.8 km
- Tilghman Island Marina - 4 min drive - 3.8 km
- Phillips Wharf Environmental Center - 5 min drive - 3.8 km
- Tilghman Watermen’s Museum - 5 min drive - 4.8 km
Getting around
Restaurants
- Two if by Sea - 5 min drive
- Gina’s @ The Bridge - 4 min drive
- Blue Heron Coffee - 21 min drive
- Tickler's Crab Shack and Restaurant - 5 min drive
- Bridge Restaurant - 4 min drive
Frequently asked questions
About the host
Hosted by Doris Price, Homeowner, Overlook on Dun's Cove waterfront vacation home
Dun’s Cove has always been a special location on the Chesapeake Bay for me. For years, my husband and I have anchored there while sailing between Oxford, Kent Island, and Annapolis. So, when Deep Harbor Farm on Dun’s Cove in Sherwood was subdivided into residential lots for sale, we jumped on the opportunity to purchase a waterfront lot of almost 3 acres. Working with local architect Margaret Garey, A.I.A. (Easton, MD), we designed and built a custom, easy care vacation home. We have spent many weekends and vacations enjoying this property which boasts an expansive view of the cove and a mature forest with a healthy mix of native evergreen and deciduous trees.
I have been a host and enjoyed sharing “Overlook on Dun’s Cove” with vacation rental guests for over 15 years. As described below under Why This Property, I have taken pride in overseeing the maintenance and periodic upgrades of the house and property, including its 220 feet of bulkheaded shoreline and deep-water pier.
It is indeed a satisfying pleasure to share our second home with vacation rental guests (several of whom book year after year) so they, too, can experience the comfort, beauty, and serenity of “Overlook on Dun’s Cove.” I look forward to hosting both new and repeat guests this year.
I have been a host and enjoyed sharing “Overlook on Dun’s Cove” with vacation rental guests for over 15 years. As described below under Why This Property, I have taken pride in overseeing the maintenance and periodic upgrades of the house and property, including its 220 feet of bulkheaded shoreline and deep-water pier.
It is indeed a satisfying pleasure to share our second home with vacation rental guests (several of whom book year after year) so they, too, can experience the comfort, beauty, and serenity of “Overlook on Dun’s Cove.” I look forward to hosting both new and repeat guests this year.
Why they chose this property
Dun’s Cove is an especially scenic and ecologically vibrant bay in the Chesapeake watershed where residents and visitors enjoy abundant crabbing, fishing, oyster beds, and exceptional birdwatching (to include the spotting of bald eagles and other rare bird species). Under the guidance of our architect, we sited and designed a custom-built weekend cottage to complement and highlight the natural beauty of the wooded lot and expansive view of the cove. Examples include: a floor-to-ceiling A-frame window wall facing the water; a wrap-around deck of over 1,000 square feet; and an open concept interior with large windows which bring the outside in whether you are working in the kitchen, eating at the dining table, or sitting around the fireplace in the living area.
The property has its own private deep-water pier with lighting, electricity, water, and a dock box that accommodates sail or power yachts up to 40-feet in length. We also provide professional mosquito and insect control so you can comfortably enjoy outdoor activities and lounging on the deck.
In 2016, working with a highly respected general contractor and a renowned kitchen specialist (Kitchen Encounters, Annapolis, MD), I completed a top-to-bottom renovation of the interior and exterior of the house. In 2022, I did an upgrade of both bathrooms, to include the showers, tub, tile, custom glass shower enclosures, toilet, and new polished chrome fixtures. Vrbo traveler reviews comment on the exceptional cleanliness and meticulous maintenance of the house and property. “Overlook on Dun’s Cove” has earned a 5-star (5.0) rating with over 100 reviews by Vrbo travelers.
The property has its own private deep-water pier with lighting, electricity, water, and a dock box that accommodates sail or power yachts up to 40-feet in length. We also provide professional mosquito and insect control so you can comfortably enjoy outdoor activities and lounging on the deck.
In 2016, working with a highly respected general contractor and a renowned kitchen specialist (Kitchen Encounters, Annapolis, MD), I completed a top-to-bottom renovation of the interior and exterior of the house. In 2022, I did an upgrade of both bathrooms, to include the showers, tub, tile, custom glass shower enclosures, toilet, and new polished chrome fixtures. Vrbo traveler reviews comment on the exceptional cleanliness and meticulous maintenance of the house and property. “Overlook on Dun’s Cove” has earned a 5-star (5.0) rating with over 100 reviews by Vrbo travelers.
What makes this property unique
Please see the full description of the amenities and unique benefits this vacation hideaway offers under the Vrbo banner and header photo above. Please contact the homeowner/host with any questions.
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