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

"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 4132.4 sq m

Popular amenities

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

Explore the area

View map
  • Place, Knapp's Narrows Marina & Inn
  • Place, Back Creek Community Park
  • Place, Tilghman Island Marina
  • Airport, Easton, MD (ESN-Easton - Newnam)

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.

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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
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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
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.
Map
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

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

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

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?

Checkout 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 holiday home is within 3 miles (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 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 148 out of 149 reviews
Rating 8 - Good. 1 out of 149 reviews
Rating 6 - Okay. 0 out of 149 reviews
Rating 4 - Poor. 0 out of 149 reviews
Rating 2 - Terrible. 0 out of 149 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host provided everything we needed. The property is beautifully decorated and the view is an ever changing picture.
Another beautiful day!
Stayed 4 nights in Oct 2025

10/10 Excellent

Jeff E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great waterfront location.secluded wooded lot and house was very nice. Great communication with host,we loved it and hope to go again. Thank you.
Stayed 3 nights in Oct 2025

10/10 Excellent

Julia C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was the perfect getaway for our family of 4. We loved the water views from inside the home and the magical light that shone through the trees throughout the day. My 11 year old son spent many hours on the dock fishing and caught 13 fish and several crabs. The house was beautifully decorated and well stocked. Don't miss the sunrise and sunset views! Would love to return again in the future!
Stayed 5 nights in Aug 2025

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

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

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

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

John W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We could not have been happier with the place. How nice to spend an early fall day watching the sun rise over Dun’s Cove. My brother and I planned to bring a boat down to do some crabbing but his vertigo caused us to scrap that and just crab off the wharf. Much to my surprise we caught almost two bushels of large crabs using traps. My wife, not a crabber, enjoyed kayaking off of West Chew Avenue in St. Michael’s. The house is beautifully furnished and everything you need is provided. There is not a thing I could say that could be improved. Okay, the dishwasher is a little confusing, but for 80 year olds practically anything beyond a sink, sponge, and a dish towel is totally befuddling to us.
Sunrise at Dun’s Cove
Stayed 6 nights in Sep 2025

10/10 Excellent

Catherine O.

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

Dun’s Cove

One of the most beautiful places I stayed at. Doris has made this house a real home. Location is perfect and loved exploring this quaint little town and surrounding areas. This house has everything you need to enjoy the stay. Highly recommend.
Stayed 3 nights in Nov 2023

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

Christopher G.

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

What a beautiful and serene property!

We had an amazing week! The house is beautiful and secluded with a gorgeous view of the water. Totally amazing place to get away from it all, relax, and recharge. We even saw a rainbow out over the water on our last night!!
Stayed 4 nights in Apr 2023

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

David G.

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

Lovely Getaway

Cute property tucked back into woods - exactly as advertised - property owner extremely attentive - glad for nice weather as the deck is the true show piece. Could use a little more comfortable furniture (living room area) and deck (lounge chairs and/or Adirondacks).
Stayed 7 nights in Jul 2023

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

Glenn G., Henrico, VA, USA

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

PERFECT PARADISE

This property could not be better in any way. It is clean, comfortable, quiet, private, well-equipped and has a wonderful view. It is the perfect getaway with a lot of class. Doris, thank you for offering such a lovely home on VRBO. I plan to return!
Stayed 7 nights in Oct 2023

10/10 Excellent

Zoe B.

Liked: Cleanliness, check-in, communication, location

The perfect spot

We absolutely loved our stay at this spectacular location , perfect for peace and relaxation. If you like to cook, you’ll be very happy in this kitchen, but there are also several great restaurants close by in St Michael’s. This place is truly a gem. Also the owner went out of her way to make sure we had an amazing anniversary celebration. Our wishlist items for this home would be to have a queen or king instead of double bed (the 2nd room only has 2 twin beds) and a comfier sofa for lounging in front of the fire would be great :) But yes these are tiny compared to all that is done so top-notch in this great getaway house.
Stayed 7 nights in Dec 2019

10/10 Excellent

Lora G.

Total Tranquility!

From the minute we arrived, we felt any stress we might have had leave our body. It is an incredibly peaceful and calming location. The wall of windows and front deck make this place. We spent a lot of time sitting on the deck enjoying the beauty of the water in front of us. On the last morning as we sipped our coffees a couple of bald eagles flew right in front of us to say good-bye. The home is in great shape, the kitchen is really well appointed and there was plenty of room for 4 of us. It is really convenient to St. Michaels - a 15 min drive as well as to Tilghman Island where we drove and rented kayaks to see a bit of the area from the water. It is true, the bed downstairs was a bit "cozy" for my 6'3" husband and almost 6' tall me - but we were so relaxed that we still slept well! We truly loved our stay at Overlook on Dun's Cove.
Stayed 3 nights in Aug 2018

10/10 Excellent

Ella J., Washington, DC

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

Relate, Relax, Release...at it's BEST!!!

This home is WON-DER-FUL!!! Any and everything you'll need and/or forgot, is in this home. I mean everything, down to baking sheets, fresh seasonings & coffee, etc...the list goes on! It literally felt like a home away from home. The property has beautiful views, dock and cool neighbors... including our friendly very cute visitor Buddy. We love to fish and there was a bunch of baby croakers out there...wish we had a boat to catch their older cousins. A lot of catch and release but it was pleasurable anyway. Caught a couple beautiful blue crabs as well. A whole lot of wishes like...I wish we rented this house for a week! Oh well, we'll just have to come back...see ya soon!
Stayed 3 nights in Jul 2021

10/10 Excellent

Paula A., Ocala

DUN'S COVE - WOW!

My family and I just finished our 10 day stay at Dun's Cove and we could not be more pleased! What a property! The location right on the river is more beautiful than any picture can convey. The beautiful dock with accommodations for boats (next time we're bringing our power boat!), the access to the water, and surrounding beauty - you never get tired of looking at the shoreline, birds, fishing boats, etc. The house is glorious! So well appointed and cared for. We have rented many vacation homes and Dun's Cove is absolutely special. The charm and sophistication of the design and furnishings lent to the comfort and coziness you want in a waterfront vacation home. The appointments are top notch - pleasing, yet not stuffy. We completely enjoyed all facets of the house and outdoor space! Another aspect of our experience at Dun's Cove was top notch is the customer service received from the rental agent and the owner. Their attention, responsiveness, professionalism rounded out our absolutely positive experience at Dun's Cove!
Stayed 10 nights in Apr 2019

10/10 Excellent

Marta O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect relaxing get away! Beautiful property right on the water! The view is phenomenal!
Stayed 3 nights in Oct 2025

10/10 Excellent

Breann W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A true Hidden Gem! The home, location, view, dock, privacy...... absolutely amazing. Doris is such a wonderful host. She checked on us to make sure we settled in and if we had any questions. I guarantee all future renters will not regret their stay at Overlook on Dun's Cove!John & Breann
Stayed 8 nights in Aug 2025

10/10 Excellent

David R.

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

Cove of Tranquility

Overlook at Dun’s Cove was, simply put, the most beautiful and tranquil place my wife and I have ever stayed—the perfect setting for our 30th anniversary getaway. The water front view is absolutely stunning, with the cabin at the edge of the woods and perfectly situated to greet the sunrise over the cove each morning. The inside of the cabin was immaculately clean, with the comfortable seating area and kitchen stylishly appointed with high-end furniture and appliances. And our host, Doris, was so kind and thoughtful, going the extra mile to ensure our stay was nothing short of perfect. The overall experience made for an anniversary my wife and I will always remember and cherish—We certainly hope to return to Overlook in the future!
Stayed 5 nights in Jul 2025

10/10 Excellent

Kelly G.

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

Great vacation

We have stayed here multiple times and love the house and location!
Stayed 4 nights in Jun 2025

10/10 Excellent

David S.

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

A lovely house on a quiet cove

This is a comfortable and up-to-date home with very upscale furnishings that sits on a quiet cove of the Chesapeake Bay. We saw herons, ospreys and comorants fishing in the mornings. Both the sunrises and sunsets were beautiful. The host was a pleasure to work with and all the instructions were very clear and helpful. I would highly recommend it to anyone looking for a waterfront vacation!
The cove just after sunrise.
The cove just after sunset.
Stayed 4 nights in Jun 2025

10/10 Excellent

derek a.

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

Great view

Wonderful place to relax a few days.
Stayed 3 nights in Apr 2025

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