Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Tilghman Island, Maryland
$651 avg/night
Minimum Stay 3 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

Night 3 nights

Min Stay

Summary:

Wake up to sweeping Chesapeake Bay views just minutes from St. Michaels. Cast a line from your private dock, sip coffee on the deck at sunrise, and end the day with spectacular sunsets over the water. Perfect for families, couples, or friends looking to relax and recharge.



Talbot County Licensure: STRN-25-51



The Space:

Tucked away on a quiet street, this light-filled home features a great room with panoramic water views and cozy coastal décor. The open layout makes it easy to spend time together, while the fully equipped kitchen has all the tools you need to prepare meals with fresh local seafood.

Step outside to your private dock for crabbing, fishing, or launching kayaks. The spacious deck is perfect for outdoor dining or simply relaxing while you watch the sun sink into the bay.



What you'll love:

- Unmatched Sunsets: “The most beautiful sunsets we’ve ever seen.”

- Private Dock: Perfect for morning coffee, fishing, or watching wildlife.

- Proximity to St. Michaels: Just minutes to charming shops, restaurants, and historic sites.

- Peaceful Location: Quiet, safe neighborhood away from the crowds.

- Fully Stocked Kitchen: Everything needed for home-cooked meals.



Escape to the shores of the Chesapeake Bay in this peaceful 3-bedroom, 2-bath home — perfect for families, couples, and friends. Located just minutes from historic St. Michaels, this waterfront getaway offers panoramic views, a private dock, and a spacious deck to enjoy unforgettable sunsets.

Whether you’re crabbing from the dock in the morning, exploring charming shops and restaurants in the afternoon, or relaxing with a glass of wine as the sun sets, this property delivers the perfect balance of relaxation and convenience.



Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.



Guest Access:

This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.



The Neighborhood:

Located in a peaceful waterfront community just minutes from restaurants, shops, and attractions in St. Michaels.



Getting Around:

Easily explore by car, bike, or on foot. Cyclists will love the scenic rides, and the property offers a secure area to store bikes.



Other Things to Note:

Firm no pet policy.

Ideal for year-round getaways — cozy by the fireplace in winter, breezy sunsets in summer

We supply a starter supply of toilet paper and paper towel.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Service Animals Only (pets Not Allowed)
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Garden
  • BATHROOMS

    2 Bathrooms Hair Dryer Shower Towels Provided
  • WORKSPACES

    Office
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Boat On Site Cycling Nearby Fishing Nearby Golf Privileges Kayak On Site
  • ENTERTAINMENT

    Games TV
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Rural Location In A Village On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Availability

Review Review

  • j s.

    Submitted Jun 8, 2026

    Stayed Jun 1, 2026

    Lovely house on the water with the most spectacular views. If you are looking for loads of peace & quiet this is your house.

  • Lisa C.

    Submitted May 19, 2026

    Stayed Apr 30, 2026

    Lovely house with fabulous view.

  • Terry K.

    Submitted May 19, 2026

    Stayed May 7, 2026

    This home was perfect setting for a four generation Mother’s Day get together, we enjoyed eating crabs, fishing, playing outside games and watching the sunset every evening.We had all of the amenities needed for a relaxing time with each other.the house was well appointed and clean.

  • Connie O.

    Submitted Apr 27, 2026

    Stayed Apr 23, 2026

    We were looking for a quiet spot for the weekend and this property delivered. The home was exactly as described and exceeded our expectations. It was well equipped, clean and very comfortable. Our host was most helpful. We highly recommend The Dock of the Bay for anyone looking for a quiet, comfortable stay with amazing sunset views. We hope to return again soon.

  • Bonnie R.

    Submitted Apr 11, 2026

    Stayed Apr 7, 2026

    Lovely home on the water with beautiful sunset views. You can sit on the dock and watch the ships go by.

  • Charles B.

    Submitted Jan 6, 2026

    Stayed Dec 22, 2025

    The condition of the house and the water views.

  • Chryssa Z.

    Submitted Oct 6, 2025

    Stayed Oct 2, 2025

    I never write reviews, but this house was worthy as it was absolutely wonderful in every way. The view is stunning. The house is super cute and well appointed. We wanted for nothing. I would definitely rent this house again.

  • Meghan M.

    Submitted Aug 27, 2025

    Stayed Aug 21, 2025

    Great location, beautiful sunsets! House was very nice and clean. Deck and dock were awesome places to hang out and just relax by the water.

  • John and Michele E.

    Submitted Aug 24, 2025

    Stayed Aug 10, 2025

    Great property!!! Absolutely would recommend!

  • Matt C.

    Submitted Aug 10, 2025

    Stayed Aug 2, 2025

    This was an amazing house in a great location. It is nicely isolated and the private dock makes for some amazing sunsets. We ate nearly every meal on the back deck. The house was decorated so nicely and well stocked. The drive into St Michael’s was only about 20min and there are several activities and restaurants.

  • Mark M.

    Submitted Aug 5, 2025

    Stayed Jul 24, 2025

    nice waterfront property, some issues with amenites (grill not clean and unsafe to use, TV not updated or usable in living room). location is close to restaurants and nearby St. Michael's. comfortable for the group of 5 including infant.

  • Michele C.

    Submitted Jul 18, 2025

    Stayed Jul 10, 2025

    Perfect location and very nice house. Delightful trip. Close to town and convenient, but private. Would highly recommend.

  • Hayley M.

    Submitted Jun 22, 2025

    Stayed Jun 19, 2025

    We absolutely loved our stay here! The house is so charming and well decorated. Everything was super clean and looked exactly like the photos. You absolutely cannot beat the view - we loved our mornings sipping coffee on the porch and the dinners watching the sun set. It’s just a short drive to St Michael’s, but we loved the quietness of the neighborhood!

  • Catherine N.

    Submitted Mar 27, 2025

    Stayed Mar 22, 2025

    The house is lovely, comfortable, clean. It is on the Chesapeake, and the back deck is just wonderful for enjoying the beautiful views of the bay and sunset. We loved the house, and the people on Tilghman Island were very nice. The house is perhaps a 20 minute drive to St. Michael's, which was a great outing for the afternoon. And, Two if by Sea, the restaurant within a couple of blocks of the house, had a wonderful breakfast. We would love to come back.

  • Suzette C.

    Submitted Feb 17, 2025

    Stayed Feb 13, 2025

    What a wonderful experience! A relaxing time with an amazing view! Thank you Jennifer

  • Zachary J.

    Submitted Nov 15, 2024

    Stayed Nov 11, 2024

    We had a great stay on Tilghman Island. The house was perfect with the unbelievable water view and open space layout inside. Super clean and comfortable, we enjoyed the days outside fishing on the dock, and the cozy fire inside during the nights. Also, the sunsets are unbelievable! We enjoyed biking all around the island, and morning walks to Two if by Sea for breakfast and a cup of coffee. The General Store on the island was close and convenient as well. Our host Jennifer was super communicative and responsive during the booking process and our stay. We are looking forward to returning to Tilghman Island and staying in this lovely home again.

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Total

Includes taxes and fees
$651+
View details