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Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

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Morning coffee by the water… evenings under the stars by your private fire pit.
Private dock for fishing, crabbing, kayaking, or simply soaking it all in.
Light-filled living space with fireplace & water views — perfect for cozy evenings.
Fully stocked kitchen & waterfront dining table for memorable family meals.
Wake up to tranquil water views

Reviews

10 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 6

Popular amenities

  • Barbecue grill
  • Dryer
  • Washer
  • Kitchen
  • Outdoor space
  • Parking available

Explore the area

View in a map
Tilghman Island, MD
  • Tilghman Watermen’s Museum
    ‪3 min drive‬
  • Tilghman Island Marina
    ‪5 min drive‬
  • St. Michaels Winery
    ‪34 min drive‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪57 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Single Bunk Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

2 bathrooms, 1 half bathroom

Bathroom

Toilet · Shower only

Bathroom #2

Toilet

Bathroom #3

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Kitchen
Office
Balcony
Garden
Dining area

About this property

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Summary:
Welcome to your private escape on Tilghman Island — a waterfront home with panoramic water views, a dock for boating and crabbing, and sunrises that will stay with you long after you leave. Perfect for families and groups, this 3-bedroom retreat blends modern comfort with coastal charm, offering multiple indoor/outdoor gathering spaces, a gourmet kitchen, and cozy spots to unwind. Just minutes from quaint shops, restaurants, and historic St. Michaels, it’s the perfect base for your Eastern Shore getaway.

Talbot County Licensure: STRN-23-32

The Space:
At the quiet edge of Tilghman Island, where the road ends and the water begins, you’ll find the perfect blend of relaxation and recreation. Step inside and you’re welcomed by an open floor plan that frames the Choptank River from nearly every window. The main living room invites you to gather by the fireplace or watch a movie. The fully equipped chef’s kitchen is designed for cooking, with premium appliances and abundant prep space. Multiple dining areas — indoors and on the screened porch — let you choose your view for every meal. All three bedrooms are thoughtfully furnished, each with plush bedding, and sweeping views. Outside, enjoy the private dock for boating or crabbing, relax on the deck with a good book, or gather around the fire pit as the stars come out.

Just a short drive away, explore St. Michaels’ boutique shops, waterfront dining, and maritime history — or simply stay in and savor the peace of your private waterfront haven.

What you'll love:

- Waterfront location with private dock
- Fire pit with Adirondack seating
- Kayaks and Paddle Boards
- Pet-friendly ($200 pet fee, per stay)
- Sleeps 6 comfortably: 3 bedrooms / 4 beds / 2.5 baths
- Fully equipped kitchen + coffee maker
- High-speed WiFi & smart TV for streaming

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:
Tilghman Island is a picturesque Eastern Shore gem, known for its working watermen’s culture, fresh seafood, and scenic beauty. Within minutes, you can enjoy waterfront dining, boutique shopping, and maritime history in St. Michaels — just a short drive away.

Other Things to Note:
Starter supply of paper towels, toilet paper, and basic toiletries provided.

Please bring extra supplies if you prefer more than the starter set.

Pets welcome upon approval — $200 non-refundable fee.

Quiet, residential neighborhood — respect local noise guidelines.

Property manager

Jennifer Brown
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Water view

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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
This property accepts cash
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

About the area

Tilghman

Located in Tilghman, this holiday home is on the waterfront. Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum are cultural highlights, and some of the area's attractions include Phillips Wharf Environmental Center and Chesapeake Beach Railway Museum. Take the opportunity to explore the area for outdoor excitement like cycling.
Map
Tilghman Island, MD

What's nearby

  • Tilghman Watermen’s Museum - 3 min drive - 2.1 km
  • Tilghman Island Marina - 5 min drive - 3.5 km
  • Phillips Wharf Environmental Center - 5 min drive - 3.8 km
  • Chesapeake Bay Maritime Museum - 33 min drive - 31.1 km
  • St. Michaels Winery - 34 min drive - 31.8 km

Getting around

  • Cambridge Station - 64 min drive
  • Easton, MD (ESN-Easton - Newnam) - 44 min drive

Restaurants

  • ‪Gina’s @ The Bridge - ‬4 min drive
  • ‪Two if by Sea - ‬3 min drive
  • ‪Marker Five - ‬4 min drive
  • ‪Tickler's Crab Shack and Restaurant - ‬3 min drive
  • ‪Bridge Restaurant - ‬4 min drive

Frequently asked questions

Is Waterfront 3-Bedroom Cottage and Pet Friendly pet-friendly?

No, only service animals are welcome at the property.

What time is check-in at Waterfront 3-Bedroom Cottage and Pet Friendly?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront 3-Bedroom Cottage and Pet Friendly?

Checkout is at 10:00 AM.

Where is Waterfront 3-Bedroom Cottage and Pet Friendly located?

Situated on the waterfront, this holiday home is within 2 miles (3 km) of Tilghman Watermen’s Museum, Talbot County Library Tilghman Branch and Kronsberg Park. Knapp's Narrows Marina & Inn and Phillips Wharf Environmental Center 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. 31 out of 33 reviews
Rating 8 - Good. 2 out of 33 reviews
Rating 6 - Okay. 0 out of 33 reviews
Rating 4 - Poor. 0 out of 33 reviews
Rating 2 - Terrible. 0 out of 33 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Jane M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was the perfect place for our stay. We enjoyed the beautiful views every morning. The house itself was lovely and perfect for our weekend trip. We loved the location too and took time to explore the island and town of St Michael’s.
Stayed 3 nights in Jul 2025

10/10 Excellent

Gary B.

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

An excellent vacation rental

An excellent vacation rental. The check in was easy. We had a vey relaxing stay. The house was super clean and very spacious. 2 1/2 baths so there’s plenty to share for when having guests over. Unbelievable view of the water front. Highly recommending this lovely home!
Stayed 3 nights in Jun 2025

10/10 Excellent

Karolyn J.

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

Relaxing Getaway

We had a wonderful stay on Tilghman Island at this beautiful property. The waterfront view from the house is stunning (as are the sunrises). We had fun using the kayak and walking over to Gina’s at the Bridge for lunch. It was a very relaxing stay!
Stayed 3 nights in May 2025

10/10 Excellent

Rhonda G.

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

Wonderful Vacation

This beautiful home was wonderful for our long overdue vacation - We loved our stay here very much - The town is amazing
Stayed 4 nights in Aug 2024

10/10 Excellent

Kim D.

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

Beautiful Waterfront Property

My family loved staying at this beautiful property which is even better in person. Loved all the little extra unexpected touches to provide you with the best possible stay. The location and view are absolutely perfect. This was definitely our favorite property we have rented in the area.
Stayed 3 nights in Aug 2024

10/10 Excellent

Olivia J.

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

Peaceful little oasis!

We absolutely loved staying here - it's such a peaceful spot on the water, and the house was incredibly clean and nice with well-made, cozy beds. Can't recommend enough!
Stayed 3 nights in Jun 2024

10/10 Excellent

MaryBeth G.

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

Anniversary weekend

We travel to the area every year for a long weekend for our anniversary. We stayed here last year and it was great so we booked again this year. Quiet neighborhood, terrific views. Working fire pit. Well stocked kitchen. Look forward to staying again next year.
Stayed 3 nights in Oct 2024

10/10 Excellent

Lori S.

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

Peaceful getaway

Beautiful view, beautiful home, very clean and well stocked! My family of 6 (2 adults, 3 teen boys and 1 younger boy) enjoyed 4 nights/3 days at this lovely home on Tilghman Island. The island itself is tucked away and very slow paced. We didn’t try any of the local restaurants (some were closed M-W), but there are a few limited options. There is a marina where you can rent fishing/crabbing equipment as well as book charters. We mostly fished from the dock (with very little luck) and enjoyed walking the gravel road, kayaking and paddle boarding.The home itself is recently updated and shows. We grabbed basic groceries on the way in and were pleasantly surprised to find how well stocked the kitchen was with oils, spices, dishes, etc. The beds were all clean and comfortable, although the primary bedroom mattress was a bit firmer than we’d like. The only thing I think was missing was a full length mirror or two- other than that we had everything we needed for a relaxing stay.The communication with the property manager was also very easy and she always responded in a timely manner. We had a few questions here and there and found her to be very helpful.Saint Michaels is an easy 20 minute drive from the house and a super cute town! We loved the ice cream at JoJo’s and the coffee from Eat Sprout (they also have a great assortment of baked goods/GF items). I wish we had more time to check out the other restaurants there!Overall- wonderful stay and would highly recommend.
Stayed 4 nights in Jul 2025

10/10 Excellent

Donna C.

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

Fantastic!

This property and the hospitality of the host was beyond our expectations. 10 stars!!
Stayed 3 nights in Jul 2024

10/10 Excellent

Brian D.

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

Great stay for a long weekend

My friends and I stayed here recently for an annual trip and loved the property and surrounding area. The house is immaculate, very comfortable, and has beautiful views. The location/surrounding area has a nice mix of feeling secluded but also having plenty to do nearby. Communication with Jennifer, the property manager, was very easy. Highly recommend staying here!
Stayed 3 nights in Jul 2023

10/10 Excellent

Jan K.

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

This house and location are beyond beautiful!

This was a girls weekend and the house could not have been more perfect!! The house and location are beautiful. It feels so homey with a beautiful yard, a dock, and so many areas to relax and enjoy. It is so thoughtfully decorated, the beds and bedding were very comfortable, and it is stocked with anything you could ever need. Nothing was overlooked. Tilghman Island and St Michaels are such a wonderful get away with great shopping, Inns, restaurants and bars. Be sure to do a sunset cruise!
Stayed 3 nights in Oct 2024

10/10 Excellent

MaryBeth G.

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

Yearly anniversary weekend to area

We have been staying in this area for the past 10 years. This has been our favorite place so far. Beautifully decorated, beautiful views. Fully equipped from phone charger ports to full kitchen necessities. Look forward to staying here again.
Stayed 3 nights in Nov 2023

10/10 Excellent

Kelly K.

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

Family Time

The house was the perfect place to spend the weekend with family. The view is amazing and no detail is overlooked.
Stayed 3 nights in Oct 2022

10/10 Excellent

ashley m.

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

Girls trip

This house is fabulous! It’s well appointed and very comfortable. I’d gladly rent again!
Stayed 3 nights in Jul 2023

10/10 Excellent

Berta K.

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

Beautiful Bay Views

We had a relaxing and enjoyable stay! We enjoyed spending time on the screened porch and deck overlooking the bay. The home was clean and comfortable, and kitchen was well stocked for a rental property. The decor was updated and pleasant. We recommend this property for a casual, comfortable getaway.
Stayed 4 nights in Jul 2023

10/10 Excellent

Joe F.

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

Peace and Quiet

First, the home is in a wonderful location. Spectacular water views; bald eagles flying around; and not a single human being anywhere in sight. Second, the house is advertised as being recently renovated and it shows. The interiors and furnishings are all in excellent condition. The bed and furniture were all very comfortable. We will definitely return in the future. We recommend this home for anyone looking for a quiet, restful respite from stress.
Stayed 4 nights in Sep 2024

10/10 Excellent

Heather T.

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

Beautiful!

The home was spacious, tastefully decorated, and immaculate. The backyard, right on the water, and the view alone are well worth the stay! The neighborhood and surroundings were so peaceful, just what we wanted for a stay away from the city. It is possibly the nicest rental we’ve ever stayed at and we plan to return. It was a wonderful relaxing trip!
Stayed 5 nights in Mar 2023

8/10 Good

Carol S.

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

Beautiful spot

The house is very nice, very well stocked. The views are spectacular, very close to the water. Property manager was very responsive, especially when we had a problem with the heat not working on the second floor.
Stayed 3 nights in Mar 2023

10/10 Excellent

Kevin J.

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

Loved “The Waterman”

This is an amazing property with beautiful sunrise views. It was recently renovated and is simply spectacular inside and out!! So clean! Great communication. We’ll definitely be back!
Stayed 3 nights in Oct 2022

10/10 Excellent

Rhonda R.

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

Unbelievable view

Quiet area without the crowds. Perfect for family gatherings. Nice water amenities kayak and paddle board. Water view is unrivaled. House was spotless and comfortably remodeled. Wish we had stayed longer with the Chesapeake Bay as our backyard!
Stayed 3 nights in Jun 2023

10/10 Excellent

Mary V.

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

Relaxing

The home was beautiful. Everything in the home is very updated and nicely decorated. Beds are veey comfortable. Everything you can think of in the kitchen. We spent a lot of time on the back porch and at night around the firepit. We would highly recommend this home. If you want a peaceful relaxing place. We stayed for 6 days on a girls trip. All three of us highly recommend this home. We would definitely stay again.
Stayed 6 nights in Apr 2024

10/10 Excellent

Elizabeth K., Gladwyne, PA

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

Quiet Getaway Retreat

Perfection. Beautifully renovated, tastefully decorated cottage with all the amenities! We had a wonderful stay at The Waterman. Stunning sunrises, beautiful views. A lovely screened in porch... the perfect spot for quiet relaxation or dinner with a view! Hammocks for lazy days. Fully stocked kitchen and very comfy beds. We look forward to returning again!
Stayed 3 nights in Apr 2023

10/10 Excellent

Marie B.

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

Can I buy this property???

The photos don’t do it justice. I want to live here! Each of us said the same thing - what you feel when you look out over the water - it’s magic .
Stayed 6 nights in May 2023

10/10 Excellent

Austin D., Bethesda, MD

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

Gorgeous waterfront house

This house was pretty spectacular. Super clean and well appointed. Beautiful kitchen and amazing wraparound view of the water. The view really is amazing. Jennifer Brown, the property manager was also AMAZING. She was so nice and responsive and even offered to get us groceries to have at the house prior to our stay. 100% recommend this house and working with Jennifer!
Stayed 3 nights in Jun 2023

10/10 Excellent

Kendall E.

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

Idyllic setting in the the most perfect house

Spotless, pretty and quiet - an amazing home with the harbor at your feet. A stunning view, well equipped kitchen and a clean, comfy bedrooms to lay your head at night. This house combines cottage charm with modern touches. This small island is just special and the nicest people! It was the start for us to the holiday season and we nicknamed Tilghman Island Bedford Falls! It's clear the owner takes great pride in this house. It felt like home and we plan on returning!
Stayed 3 nights in Nov 2022

About the host

Hosted by Jennifer Brown

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests