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

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Living area
Private kitchen
Living area
Room
Outdoor dining

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Outdoor barbecue
  • Balcony

Explore the area

View in a map
Tilghman Island, MD
  • Place, Tilghman Watermen’s Museum
    ‪6 min walk‬
  • Place, Kronsberg Park
    ‪14 min walk‬
  • Place, Tilghman Island Marina
    ‪2 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪46 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

2 bathrooms

Bathroom

Bathtub · Toilet · Shower only

Bathroom #2

Toilet · Shower only

Spaces

Kitchen
Office
Balcony
Garden
Dining area

About this property

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

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.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 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, service animals permitted
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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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Tilghman

Located in Tilghman, this holiday home is in a rural area and on the waterfront. St. Michaels Museum and Spocott Windmill are local landmarks, and some of the area's attractions include Phillips Wharf Environmental Center and Chesapeake Bay Maritime Museum. Chesapeake Beach Railway Museum and Chesapeake Beach Water Park are also worth visiting. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
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Map
Tilghman Island, MD

What's nearby

  • Tilghman Watermen’s Museum - 6 min walk - 0.6 km
  • Talbot County Library Tilghman Branch - 11 min walk - 1.0 km
  • Kronsberg Park - 14 min walk - 1.2 km
  • Tilghman Island Marina - 2 min drive - 2.1 km
  • Phillips Wharf Environmental Center - 3 min drive - 2.5 km

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 43 min drive

Restaurants

  • ‪Two if by Sea - ‬6 min walk
  • ‪Gina’s @ The Bridge - ‬2 min drive
  • ‪Tickler's Crab Shack and Restaurant - ‬11 min walk
  • ‪Marker Five Waterfront Dining - ‬3 min drive
  • ‪Bridge Restaurant - ‬2 min drive

Frequently asked questions

Is Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views pet-friendly?

No, only service animals are welcome at the property.

How much does it cost to stay at Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views?

As of 5 May, 2026, prices found for a 1-night stay for 2 adults at Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views on 21 Jun, 2026 start from S$509, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views?

On-site parking is available at the property.

What time is check-in at Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views?

Check-in begins at 4:00 PM.

What time is check-out at Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views?

Checkout is at 10:00 AM.

Where is Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views located?

Situated on the waterfront, this holiday home is steps away from Chesapeake Bay and Northern Chesapeake Bay. Tilghman Watermen’s Museum and Talbot County Library Tilghman Branch are also within 15 minutes.

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. 12 out of 13 reviews
Rating 8 - Good. 1 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Bonnie R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely home on the water with beautiful sunset views. You can sit on the dock and watch the ships go by.
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

John and Michele E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property!!! Absolutely would recommend!
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Charles B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The condition of the house and the water views.
Stayed 11 nights in Dec 2025
Verified

10/10 Excellent

Meghan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Michele C.

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

Fabulous vacation

Perfect location and very nice house. Delightful trip. Close to town and convenient, but private. Would highly recommend.
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Hayley M.

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

Beautiful Property!

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!
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Matt C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Aug 2025
Verified

10/10 Excellent

Chryssa Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Suzette C.

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

Beautiful and immaculate!!

What a wonderful experience! A relaxing time with an amazing view! Thank you Jennifer
Stayed 3 nights in Feb 2025
Verified

8/10 Good

Mark M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Catherine N.

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

Spring around the corner

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.
Stayed 4 nights in Mar 2025
Verified

10/10 Excellent

Zachary J.

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

Our Perfect Stay

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.
Stayed 3 nights in Nov 2024
Verified

10/10 Excellent

Connie O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Apr 2026

About the host

Hosted by Jennifer Brown

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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