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Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

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"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
View of Dun's Cove and property from private pier, accommodates boats up to 40'
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Relax, enjoy the fire, and splendid views in the cherry lounging furniture
Scenic dining with waterfront and woodland views you won't tire of seeing
Reviews
10 out of 10 Exceptional
2 bedrooms2 bathroomsSleeps 4132 sq m

Popular amenities

  • FireplaceFireplaceFireplace
  • Free WiFiFree WiFiFree WiFi
  • WasherWasherWasher
  • DryerDryerDryer
  • Outdoor spaceOutdoor spaceOutdoor space
  • Air conditioningAir conditioningAir conditioning

Check out the area

Map
Sherwood, MD
  • Popular LocationTilghman Watermen’s Museum5 min drive
  • Popular LocationChesapeake Bay Maritime Museum20 min drive
  • Popular LocationSt. Michaels Winery20 min drive
  • AirportSalisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)91 min drive

Rooms & beds

2 bedrooms (sleeps 4)

Master

Upstairs Bedroom

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 happily note their productive catches in our Guest Book.) 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.

New upgrades over and above a recent top-to-bottom renovation assure luxury, comfort, and functionality that will delight the most discriminating vacation rental guests. The living and dining areas, master bedroom, and home office/den have newly installed red oak hardwood flooring. Stylish wool rugs define different areas in the open concept living space. The master bedroom has a new 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. Additional remodeling of these bathrooms, completed in 2022, features new 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). Updated bathroom photos will be posted shortly.

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 $260 for January 8 - February 28, 2023; $275 for March 1 - May 14, 2023; $325 for May 15- October 15, 2023 (peak season); and $275 for October 16, 2023 - January 6, 2024.

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-22-16.

Property manager

Doris Price, Homeowner, Overlook on Dun's Cove waterfront vacation home
Premier Host
Premier Host

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space

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
The Rental Agreement contains the House Rules Talbot County requires for vacation rentals, to which the Traveler and Booking Request must comply.
All reservations are subject to owner screening and approval before they become final. This will occur within 24 hours of the booking.
A $75.00 cancellation fee may be applied to a cancelled reservation unless the Traveler re-books the property promptly (see Rental Agreement).

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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-22-16

We should mention

A car is required for transportation to and from this property

About the area

Sherwood

Located in Sherwood, this vacation home is in a rural area and on the waterfront. Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum are cultural highlights, and some of the area's landmarks include Avalon Theatre and Choptank River Lighthouse. Traveling with kids? Consider Chesapeake Beach Railway Museum and Chesapeake Beach Water Park. Be sure to check out the area's animals with activities such as game walks and birdwatching.
Map
Sherwood, MD

What's nearby

  • Phillips Wharf Environmental Center - 4 min drive
  • Tilghman Watermen’s Museum - 5 min drive
  • Chesapeake Bay Maritime Museum - 20 min drive
  • St. Michaels Winery - 20 min drive
  • U.S. Naval Academy - 93 min drive

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 39 min drive

Restaurants

  • Marker Five - 4 min drive
  • Two If By Sea - 5 min drive
  • Tickler's Crab Shack - 5 min drive
  • Blue Heron Coffee - 21 min drive
  • Harrison's Chesapeake House - 5 min drive

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 117 out of 118 reviews" "
Rating 8 - Good. 1 out of 118 reviews" "
Rating 6 - Okay. 0 out of 118 reviews" "
Rating 4 - Poor. 0 out of 118 reviews" "
Rating 2 - Terrible. 0 out of 118 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Sheri W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfectly Peaceful
This property provided the perfect, peaceful weekend escape for my husband and I. Dun’s Cove proved to be the best location to stay in the area with all the attractions and amenities nearby yet, we were always welcomed back by the tranquility of this property nestled along the shore. The views from within the home enhanced the feeling of being outdoors at all times and the added bonus of a wood burning fireplace truly made our time special. Whether you are in the area and need a place to stay or as a destination home, we would highly recommend renting this property.
Stayed 3 nights in Dec 2021

10/10 Excellent

Lindsay H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful getaway
I've been here several times and it never fails to be a wonderful, beautiful, and peaceful getaway. It's close enough to St. Michaels for shopping and dining, but is cozy even on cold days when you can light a warm fire and enjoy the views.
Stayed 3 nights in Mar 2024

10/10 Excellent

allyson C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Happy Place!
After my 4th or 5th stay, I am still anxious to book again this year! From the calm that takes over you when taking in the view to the chef's kitchen where we created spectacular dinners, you will want for nothing at The Overlook!
Stayed 3 nights in Feb 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Almost Heaven
Beautifully updated A-frame with a gorgeous view of the water. Short distance from St. Michael's, shops and restaurants. Lovely.
Stayed 3 nights in Jan 2024

10/10 Excellent

Brian O., Los Altos, California

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Home on Dunn's Cove
We loved this beautiful two bed/two bath home on Dunn's Cove on the Eastern Shore of Maryland. The home is well appointed with everything to cook with and to be comfortable. The view of the water and trees is spectacular. Our host Doris thought everything. Communication was very helpful and thorough. A short drive to the very cute village of St. Michaels. We hope to be able to come back sometime. Highly recommended!
Stayed 4 nights in Jan 2024

About the host

Hosted by Doris Price, Homeowner, Overlook on Dun's Cove waterfront vacation home

Host profile image
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.

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. Last year (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 90 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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