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

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

"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 41425 sq ft

Popular amenities

  • Dryer
  • Washer
  • Fireplace
  • Barbecue grill
  • Kitchen
  • Parking available

Explore the area

Map
Sherwood, MD
  • Tilghman Watermen’s Museum
    ‪5 min drive‬
  • Chesapeake Bay Maritime Museum
    ‪20 min drive‬
  • St. Michaels Winery
    ‪20 min drive‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪39 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Master

1 Queen Bed

Upstairs Bedroom

2 Twin 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.

Property manager

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

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
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
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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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).

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-24-56, STRN-22-16

We should mention

A car is required for transportation to and from this property

About the neighborhood

Sherwood

Located in Sherwood, this vacation 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. 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 - 3.3 km
  • Tilghman Watermen’s Museum - 5 min drive - 4.0 km
  • Chesapeake Bay Maritime Museum - 20 min drive - 19.3 km
  • St. Michaels Marina - 20 min drive - 19.2 km
  • St. Michaels Winery - 20 min drive - 19.6 km

Getting around

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

Restaurants

  • ‪Blue Heron Coffee - ‬21 min drive
  • ‪Two If By Sea - ‬5 min drive
  • ‪Marker Five - ‬4 min drive
  • ‪Tickler's Crab Shack and Restaurant - ‬5 min drive
  • ‪Bay Hundred Restaurant - ‬4 min drive

Frequently asked questions

Is Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels?

Check-in begins at 4:00 PM.

What time is check-out at Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels?

Check-out is at 11:00 AM.

Where is Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels located?

Situated on the waterfront, this vacation home is within 3 mi (5 km) of Knapp's Narrows Marina & Inn, Back Creek Community Park, and Kronsberg Park. Phillips Wharf Environmental Center and Tilghman Island Marina are also within 3 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 136 out of 137 reviews
Rating 8 - Good. 1 out of 137 reviews
Rating 6 - Okay. 0 out of 137 reviews
Rating 4 - Poor. 0 out of 137 reviews
Rating 2 - Terrible. 0 out of 137 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Katharine K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Short stay

Very nice
Stayed 3 nights in Apr 2025

10/10 Excellent

Susan F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Simply Perfect

Second stay at this wonderful spot by the water. Quiet area, private, cozy, and clean. Excellent communication from the host. Simply perfect!
Stayed 6 nights in Dec 2024

10/10 Excellent

Edward S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dun`s Cove getaway

Excellent location for privacy & view !!!
Stayed 4 nights in Sep 2024

10/10 Excellent

Nancy C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful experience!

Great location! Beautiful scenery! Highly recommend!
Stayed 3 nights in Oct 2024

10/10 Excellent

Jan R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Superb

Peaceful and beautiful location. This accommodation is very well appointed. Owner was very helpful. My husband and I had a lovely getaway here. We’ll be back again soon.
Stayed 4 nights in Dec 2024

10/10 Excellent

Ruth F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Experience

We had a wonderful long weekend in the house. As it was freezing outside, we were inside most of the time, and the house delivered. The views are gorgeous, the whole home tastefully furnished, the fireplace a gem. Just as wonderful was Doris's willingness to communicate and address issues we hadn't even thought of, and Shannon's availability help when we needed it (e.g., it snowed). We loved our time here.
Stayed 3 nights in Jan 2025

10/10 Excellent

allyson C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Never get tired of that VIEW!

Just returned from my 6th (?) stay at this property and I continue to be mesmerized by the expansive views. While we didn't get outside much due to the frigid temps and howling winds, this was our most relaxing visit! We cooked all of our meals, had a nice fire each day, read, caught a few old movies on TV and just exhaled. This home has EVERYTHING you need to totally unwind. Thank you again Doris, for providing the perfect sanctuary!
Stayed 3 nights in Jan 2025

10/10 Excellent

Christine A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful property

We had a wonderful stay at Overlook on Dun’s Cove. We brought our boat and kept it at the dock with no issues, and enjoyed our stay. The owner was accessible as needed during our visit.
Stayed 10 nights in Sep 2024

10/10 Excellent

Lela B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Place

This home is so cozy and inviting. Have been coming here for the past 6 years and love it every time I come. The host goes above and beyond to please her guest. Definitely a 10
Stayed 4 nights in Sep 2024

10/10 Excellent

Matt L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house. Great location

Very nicely appointed home in a great location. You can’t beat the views for sunrise and sunset. Very private and quiet. We will try to return for another visit.
Stayed 7 nights in Jul 2024

10/10 Excellent

Michael G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Deck

House great Beautiful spot Only suggestion is more comfortable lounges on geck
Stayed 4 nights in Sep 2024

10/10 Excellent

Courtney H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We loved it!

The property was great! It was exactly as pictured, very clean and well appointed. The host was very nice and you can tell they care about the property and that their guests enjoy their stay. The views from the deck were great, we really enjoyed our stay!
Stayed 4 nights in Jun 2024

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

A slice of heaven

Doris thank you so very much for sharing your amazing home with us. We have stayed in many places over our years, however Dun Cove is in a league of its own. We will return.
Stayed 4 nights in Aug 2024

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

Arnel C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Getaway

The house is situated in an idyllic setting surrounded by lush greenery and stunning views. The living and dining areas were furnished with stylish mid-century modern pieces, creating a sophisticated atmosphere. The house was equipped with everything we needed for a comfortable stay. Thank you for providing such a wonderful experience.
Stayed 4 nights in Aug 2024

10/10 Excellent

Lew H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quite getaway

Close to many interesting and historic places on the bay. A ferry ride to Oxford, 5 minutes to Tilghman, 15 to St. Michael's, Wittman docks watermen unloading their catch, Claiborne's ferry dock last used in 1952. Replaced by the bridge. Many dining options and a great kitchen if you prefer to cook. Chesapeake Landing 8 miles north on 33, fresh caught crab and oysters, dine in or takeout. A favorite of the locals.
Stayed 7 nights in Sep 2024

10/10 Excellent

Patrick G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing bay stay

Nice and well maintained vacation home, loved fishing off the pier every day. Quiet spot helped recharge body and soul , would visit again
Stayed 4 nights in Jun 2023

10/10 Excellent

Tammy W.

Lovely home, beautiful setting.

Enjoyed our stay, lots of little touches made it a special experience.
Stayed 2 nights in May 2018

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

Edward S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dunn`s Cove

Ideal location for peace and quiet without commercial traffic on the bay.
Stayed 4 nights in Sep 2023

10/10 Excellent

Sam F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Repeat stay

This was our third year to stay in this house. The size and location is perfect for us. Everything in order. Highly recommend.
Stayed 3 nights in May 2024

10/10 Excellent

Scott D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Overlook on Dun Cove Excellent

We totally enjoyed our stay at this property and wouldn't hesitate to return. Great location and well appointed with excellent views.
Stayed 7 nights in Jul 2020

10/10 Excellent

Blair M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house in a great location

The house is beautiful and the view cannot be beat. Was great to be so close to the town of St. Michaels and all that is has to offer. Would definitely consider staying here again!
Stayed 3 nights in Nov 2021

10/10 Excellent

Susan F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Stay

Wonderful spot that felt like home. Clean, comfortable, and well-appointed, and perfect communication from our host. Many thanks! Looking forward to returning...
Stayed 4 nights in Dec 2023

10/10 Excellent

ken j.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time on the Cove

Truly amazing. Wonderful view, perfect for lounging on the expansive front deck, or on the dock. Private and peaceful. Was a joy to work in the most well appointed kichen. Views of eagles and osprey a special bonus! Easy driving access to many Chesapeake Bay area highlights.
Stayed 8 nights in Apr 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. 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.

Languages:

English

Premier Host

They consistently provide great experiences for their guests