Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
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.
Add dates for prices
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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
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 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. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Chesapeake Bay Maritime Museum - 28 min drive - 32.1 km
St. Michaels Winery - 29 min drive - 32.8 km
Saint Michaels Village - 30 min drive - 34.2 km
Getting around
Cambridge Station - 64 min drive
Easton, MD (ESN-Easton - Newnam) - 44 min drive
Restaurants
Two if by Sea - 3 min drive
Gina’s @ The Bridge - 4 min drive
Tickler's Crab Shack and Restaurant - 3 min drive
Marker Five Waterfront Dining - 4 min drive
Big Mack's Kitchen & Dock Bar - 4 min drive
Frequently asked questions
Is Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets?
As of 10 May 2026, prices found for a 1-night stay for 2 adults at Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets on 11 May 2026 start from AU$723, 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 Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets?
On-site parking is available at the property.
What time is check-in at Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets?
Check-in begins at 4:00 PM.
What time is check-out at Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets?
Checkout is at 10:00 AM.
Where is Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets located?
Situated on the waterfront, this holiday home is within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay. Tilghman Watermen’s Museum and Talbot County Library Tilghman Branch are also within 2 miles (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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.
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!
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!
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!
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.
Kim D.
Stayed 3 nights in Aug 2024
Response from VrboOwner on 27 Aug 2024
Kim,
Thank you for choosing Waterman. We are so glad to know you enjoyed your stay. Thank you for the super feedback! Please join us again soon.
Jennifer
Flaneur, the vacation co.
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!
Stephanie E.
Stayed 6 nights in Oct 2025
Response from VrboOwner on 27 Oct 2025
Thank you for the wonderful review.
We are so glad that you enjoyed your stay.
We apologize for any inconvenience the door or screen may have caused as they are being addressed but are a work in progress.
Please join us again and receive a 10% discount for your troubles.
Jennifer
Flaneur, the vacation rental co.
We loved all the renovations! The place was beautiful inside, and breathtaking view/water access outside! Jennifer thought of all the little details that matter..sheets, towels, trash bags, toilet paper, paper towels, soap ect… The home was very warm and inviting.
The house was the perfect place to spend the weekend with family. The view is amazing and no detail is overlooked.
Kelly K.
Stayed 3 nights in Oct 2022
Response from VrboOwner on 15 Aug 2023
Kelly,
Thank you for joining us. We are very happy that you enjoyed yourselves and we look forward to hosting you again in the near future! New Years is always fun on the Shore!
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!
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.
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.
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.
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!
Heather T.
Stayed 5 nights in Mar 2023
Response from VrboOwner on 15 Aug 2023
Heather,
Thank you!
We are so happy that you had such a great experience while staying at the Waterman.
It is important to us that our guests love the property as much as we do.
We look forward to having you stay with us again in the near future.
Jennifer
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.
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!
Kevin J.
Stayed 3 nights in Oct 2022
Response from VrboOwner on 15 Aug 2023
Kevin,
Thank you for joining us at the Waterman.
We are so pleased you enjoyed the property and the incredible sunrises.
Summer season has started to book. Please let us know when you are ready to visit with us again.
Jennifer
Flaneur, the vacation rental company
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!
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!
Jan K.
Stayed 3 nights in Oct 2024
Response from VrboOwner on 10 Oct 2024
Jan,
We are so glad you all enjoyed your time at the Waterman.
It's a special home in a special spot.
We hope you and the girls will join us again soon.
Jennifer
Flaneur, the vacation rental co.
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!
Elizabeth K.
Stayed 3 nights in Apr 2023
About the host
Hosted by Jennifer Brown
Languages:
English
Premier Host
They consistently provide great experiences for their guests