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Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Riverside holiday home with kitchen and balcony

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Property grounds - Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets (Tilghman Island)
Interior - Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets (Tilghman Island)
Interior - Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets (Tilghman Island)
Dining - Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets (Tilghman Island)
3 bedrooms, iron/ironing board, WiFi, bed sheets - Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets (Tilghman Island)
Wake up to the serene waters of Harris Creek at this 3 bedroom, 2.5 bathroom home. With its expansive living area and panoramic views, you'll feel like you're working from paradise with 300mb/s Internet and great wifi - perfect for a couples' or friends' getaway.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms3 bathrooms

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning
  • Outdoor space

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

Property amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Electric car charging station on site
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Towels provided

Entertainment

  • Games
  • TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • On a river
  • On the waterfront

Things to do

  • Kayak
  • Optional golf privileges
  • Cycling nearby
  • Fishing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Electric car charging station
  • Garden

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

No events allowed

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
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

62c2daf68de6ff0035da2b31

About the area

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. Visit our Tilghman travel guide
View more Holiday homes in Tilghman
Map
Tilghman Island, MD

What's nearby

  • Boats docked in the harbor, in St. Michaels, Maryland.
    St. Michaels Marina
    27 min drive - 31.1 km
  • Hooper strait lighthouse 1879. Now in the Chesapeake Maritime museum St Michaels Md #maryland #StMichaels #HooperStraitLighthouse
    Chesapeake Bay Maritime Museum
    27 min drive - 31.1 km
  • Tilghman Watermen’s Museum
    3 min drive - 2.1 km
  • 1879 Hooper Straight Lighthouse
    27 min drive - 31.1 km
  • St. Michaels Winery
    28 min drive - 31.8 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
  • Bay Hundred Restaurant
    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 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).

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Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 34 out of 36 reviews
Rating 8 - Good. 2 out of 36 reviews
Rating 6 - Okay. 0 out of 36 reviews
Rating 4 - Poor. 0 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

10

Cleanliness

10

Location

Reviews

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

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

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

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

Bradley N.

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

Amazing Place!

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.
Stayed 3 nights in Jul 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

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

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

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

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

Kathy L.

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

It's Everything and More.....

We had an amazing stay! This home has anything and everything you will need. The property is on a quiet street and being on the water is always calming. I wish there was a way to easily get into the water (full disclosure, I did NOT reach out to ask if there was a ladder or anything else, as I was completely off my device for the entirety of our stay). We loved playing corn hole every night! St. Michael's is so close and we found ourselves heading downtown, to the farmer's market and out shopping and eating every day! The beds were comfortable and having soap and lotion at every sink was wonderful!! Not to mention the body wash, shampoo and conditioner in both showers! We will most definitely be returning to this fabulous home again. You should check it out, for sure!
Stayed 3 nights in May 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

Joe F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We love this property and most definitely plan to stay there again in the future.
Stayed 4 nights in Sep 2025

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

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

Stephanie E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 6 nights in Oct 2025

8/10 Good

Tracy D., PA

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

Beautiful, peaceful home

the location of this home is wonderful......total peace and quiet.
Stayed 3 nights in Jun 2023

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

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

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

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