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

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A spacious living room with a large white sofa, a dining area with a table and chairs, and a ceiling fan.
A waterfront property with a wooden dock, a rocky breakwater, and two houses with large windows and a porch.
A modern kitchen with white cabinets, stainless steel appliances, and a large island.
A spacious living room with a high ceiling, a fireplace, a large TV, and a staircase leading to an upper level.
A modern kitchen with white cabinets, a black cabinet, and a dining area with a wooden table set for four.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Scenic water view
    Relax and unwind with top-rated water views, offering a scenic experience.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Chesapeake Bay

Popular amenities

  • Balcony
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Onsite parking available
  • Washing machine

Explore the area

View map
Tilghman Island, MD
  • Place, Northern Chesapeake Bay
    ‪1 min walk‬
  • Place, Tilghman Watermen’s Museum
    ‪6 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

Add dates for prices

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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

  • Northern Chesapeake Bay - 1 min walk - 0.1 km
  • Tilghman Watermen’s Museum - 6 min walk - 0.6 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

  • ‪Big Mack's Kitchen & Dock Bar - ‬3 min drive
  • ‪Gina’s @ The Bridge - ‬2 min drive
  • ‪Tickler's Crab Shack and Restaurant - ‬11 min walk
  • ‪Two if by Sea - ‬6 min walk
  • ‪Marker Five Waterfront Dining - ‬3 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 4 November 2026, prices found for a 1-night stay for 2 adults at Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views on 7 March 2027 start from NZ$4,340, 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.
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Rating 10 - Excellent. 23 out of 25 reviews
Rating 8 - Good. 2 out of 25 reviews
Rating 6 - Okay. 0 out of 25 reviews
Rating 4 - Poor. 0 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This vacation spot was amazing. The house was beautiful and had everything and more. We are already talking about planning our next trip to stay. Wish we could have stayed longer for sure. House was nice and close to St Michael and gift shops and restaurants. Amazing vacation
Stayed 3 nights in Jul 2026
Response from VrboOwner on 1 August 2026
WE HOPE YOU HAD A GREAT STAY AND MADE A TON OF WONDERFUL MEMORIES! IT WAS A PLEASURE TO HAVE YOU JOIN US. JENNIFER FLANEUR, THE VACATION RENTAL CO.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely house with fabulous view.
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, well-maintained home with fantastic waterfront views! A wonderful spot for relaxing and enjoying quiet time with family and friends. Our host was very responsive to our requests.
Stayed 3 nights in Jul 2026
Response from VrboOwner on 1 August 2026
Thank you, Marcy. Glad to know you all enjoyed. Please join us again soon. Jennifer
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a delightful place on the water close enough to good food and shopping.Gorgeous sunset views and warm cozy feeling looking out at the bay on a rainy day.Clean and well appointed. Timely response to internet issues so everyone could watch their favorite college football games.
Stayed 4 nights in Sep 2026
Response from VrboOwner on 12 October 2026
Thank you, Vera. So great to hear you enjoyed your stay and we would love to host you again.
Verified review

10/10 Excellent

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

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at this waterfront home! The views were absolutely beautiful, especially at sunset. The property was very well maintained, tastefully decorated, and had lovely furnishings throughout. The kitchen was well equipped with everything we needed. We spent hours relaxing on the deck overlooking the water, making it the perfect spot for a girls’ weekend. We would definitely stay here again and highly recommend it!
Stayed 3 nights in Jul 2026
Response from VrboOwner on 3 August 2026
It was great to host you Heather and friends. They were a pleasure and we look forward to them joining us again. Jennifer Flaneur, the vacation rental co.
Verified review

10/10 Excellent

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
Response from VrboOwner on 23 April 2026
Hello Bonnie, Blue Crab does have some wonderful views. We are glad you enjoyed your stay and look forward to you returning. Jennifer Flaneur, the vacation rental co.
Verified review

10/10 Excellent

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 review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our week on Tilghman Island at Dock of the Bay was everything we could have expected and so much more! The house was a beautiful retreat sitting right on the bay, comfortably decorated,relaxing, and restful with the most amazing views. The sunsets were breathtaking. The quietness was so peaceful and watching all the various ships and boats pass was a highlight for us. Fishing off the private dock was another relaxing experience. We can't wait to return and stay at Dock by the Bay!!!!
Stayed 5 nights in Jul 2026
Response from VrboOwner on 1 August 2026
WE ARE SO HAPPY YOU HAD A GREAT STAY AND MADE A TON OF WONDERFUL MEMORIES! IT WAS A PLEASURE TO HAVE YOU JOIN US. JENNIFER FLANEUR, THE VACATION RENTAL CO.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The condition of the house and the water views.
Stayed 11 nights in Dec 2025
Response from VrboOwner on 23 April 2026
Hi Charles We would love to host you again now that the weather is warming up. Jennifer Flaneur, the vacation rental co.
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Response from VrboOwner on 23 June 2025
Thank you, Haley! It was great to have you join us and we look forward to having you join us again soon. Jennifer
Verified review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 7 October 2025
Thank you, Chryssa, for the stellar review. We love Dock of the Bay, and it was great to host you. We look forward to you joining us again. Jennifer Flaneur, the vacation rental co.
Verified review

10/10 Excellent

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
Response from VrboOwner on 4 March 2025
Suzette, We are very pleased to know you enjoyed your stay. We look forward to hosting you again in the future. Jennifer Flaneur, the vacation rental co.
Verified review

8/10 Good

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
Response from VrboOwner on 6 August 2025
Thank you for joining us at Dock of the Bay. Guest experience is of the utmost importance to us, and we were happy to send a team member to assist you. We sincerely apologize for any inconvenience that Mark may have encountered during his stay. As stated in the listing, the TV is a smart TV, and the connection cables can be found just under the table beneath the TV. The grill situation has been corrected, and the guest was compensated accordingly. We hope Mark will join us again at one of our other properties as we would like to offer a discounted rate. Jennifer Flaneur, the vacation rental co.
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely loved the house which was very well equipped and beautiful. Jennifer was very helpful and quick to respond to any questions.
Stayed 3 nights in Jun 2026
Response from VrboOwner on 6 July 2026
Thank you for joining us Lynne. We look forward to you returning. Jennifer Flaneur, the vacation rental co.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was just as advertised. The property is beautiful and the house was clean and comfortable. Looking forward to renting again!
Stayed 4 nights in Jun 2026
Response from VrboOwner on 6 July 2026
Terrific views and a peaceful spot. Thank you for joining us.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We very much enjoyed our stay here. The house was spotless, and smelled very clean upon arrival. Beautiful warm cozy home with an amazing view. Everything you’d need was provided, such as linens and stocked kitchen for cooking. We would come again and highly recommend for a relaxing home away from home!
Stayed 3 nights in Jun 2026
Response from VrboOwner on 6 July 2026
Thank you, Holly. Always something to do in St Michaels...come back soon
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely house on the water with the most spectacular views. If you are looking for loads of peace & quiet this is your house.
Stayed 7 nights in Jun 2026
Response from VrboOwner on 16 June 2026
Spectacular views, peace and quiet. We couldn’t have said it better. Thank you for joining us and we look forward to having you come back soon. Jennifer Flaneur the vacation rental co.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Aug 2026
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