Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island, Maryland
$530 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:

Escape to Tilghman Island, a historic Chesapeake Bay community known for its working waterfront, friendly locals, and quiet pace of life. This charming cottage offers a comfortable, relaxing retreat for guests looking to unplug, unwind, and experience an authentic island stay.



Talbot County Licensure: STRN-25-35



The Space:

The home is thoughtfully furnished to feel welcoming and easy, with cozy living spaces, a fully equipped kitchen, and comfortable bedrooms designed for real rest. Whether you’re visiting for a quiet getaway, a boating or fishing trip, or a peaceful stay with your dog, this cottage provides an ideal home base.



Location Highlights:

Tilghman Island is not a resort destination — it’s a true Chesapeake Bay island, and that’s exactly what makes it special.



Guests love the area for:

-Marinas, docks, and working boats

-Local seafood restaurants and island bars

-Excellent fishing, crabbing, and boating

-Quiet roads ideal for walking and biking

-Easy access to St. Michaels and Easton



🛏️ Sleeping & Comfort

The cottage is set up for comfort and longer stays.

- Comfortable bedrooms with quality mattresses

- Fresh linens and extra pillows provided

- Peaceful nights thanks to the island’s quiet setting



🍳 Kitchen & Dining

- Enjoy the convenience of a fully equipped kitchen during your stay.

- Cookware and essential kitchen items provided

- Coffee maker and basics included

- Dining area suitable for meals or remote work



Perfect for preparing fresh local seafood or enjoying relaxed mornings at home.



🐾 Pet-Friendly

-Well-behaved pets are welcome so the whole family can enjoy island life.

- Pet fee applies

- Quiet roads and open areas nearby for walks



Pet-friendly homes on Tilghman Island are limited and in high demand.



If you’re seeking crowds, this isn’t the place. If you’re seeking calm, character, and coastal charm, you’ve found it.



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.

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

Feature Features

  • PETS

    Pet Friendly Service Animals Exempt From Fees
  • 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

    Electric Car Charging Station On Site Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Garden
  • BATHROOMS

    2.5 Bathrooms Hair Dryer Shower Towels Provided
  • WORKSPACES

    Office
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Golf Privileges Kayak On Site
  • ENTERTAINMENT

    Games TV
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Village On The River 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

  • Julie K.

    Submitted Jun 9, 2026

    Stayed Jun 4, 2026

    This was an exceptional property. The outdoor space was beautiful. Everything inside and outside was exactly as described. The house was clean, well stocked and nicely decorated. Beds were comfortable,kitchen had everything we needed and we wish we could have stayed longer. The host was very quick to respond to a few questions that we had. It was dog friendly, and the pups had a great time. We are looking forward to coming back again.

  • Joe F.

    Submitted May 23, 2026

    Stayed May 18, 2026

    Beautiful home in a beautiful location. We are repeat visitors and plan to visit again.

  • Steph R.

    Submitted May 2, 2026

    Stayed Apr 28, 2026

    Very clean, lovely bedding...slept so good.Waterfront was wonderful.I messaged the host to advise the screen on porch was pulled away on the top, not sure if message was received.

  • Laura M.

    Submitted Apr 13, 2026

    Stayed Apr 9, 2026

    The house was in a great location.the kitchen was fully equipped, and the house was very pet friendly. so beautiful and relaxing, right on the water!

  • Pierce S.

    Submitted Apr 10, 2026

    Stayed Apr 5, 2026

    Will stay again when in town!

  • Stephanie E.

    Submitted Oct 12, 2025

    Stayed Oct 6, 2025

    We had a good time at this property, pier is great for fishing and crabbing. Beds were comfortable, kitchen was equipped with everything we needed. The view from the living room was beautiful. The host was great at communicating to me fast and took care of all our needs! One thing that was a bit annoying was the screened in porch door was broken , the door wouldn't stay open when latched with the cylinder and wouldn't close securely, also the screen on the back of the porch was ripped. Silly things that seemed like a nice property would have fixed and not tried to tape back together. But overall a great weeks stay for us!

  • Joe F.

    Submitted Sep 19, 2025

    Stayed Sep 15, 2025

    We love this property and most definitely plan to stay there again in the future.

  • Jane M.

    Submitted Aug 14, 2025

    Stayed Jul 31, 2025

    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.

  • Lori S.

    Submitted Jul 24, 2025

    Stayed Jul 20, 2025

    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.

  • Gary B.

    Submitted Jul 6, 2025

    Stayed Jun 27, 2025

    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!

  • Karolyn J.

    Submitted May 18, 2025

    Stayed May 15, 2025

    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!

  • MaryBeth G.

    Submitted Oct 30, 2024

    Stayed Oct 24, 2024

    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.

  • Jan K.

    Submitted Oct 6, 2024

    Stayed Oct 3, 2024

    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!

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Total

Includes taxes and fees
$532+
View details