See all properties
Entire home

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Photo gallery for Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Charming Tilghman Island cottage offering a peaceful Chesapeake Bay escape
Cozy living space perfect for relaxing after a day exploring Tilghman Island
Comfortable bedroom with fresh linens for a restful island night’s sleep
Fully equipped kitchen for easy meals
Dining space ideal for meals, remote work, or slow island mornings

Reviews

10 out of 10, Loved by Guests
Top 10% based on
3 bedrooms2+ bathroomsSleeps 6

Popular amenities

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

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 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Toilet

Spaces

Kitchen
Office
Balcony
Garden
Dining area

About this property

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

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Spacious home with expansive backyard and pool for ultimate relaxation.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
10.0 out of 10, Exceptional, (22 reviews)
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed
default

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

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.
View more Holiday homes in TilghmanOpens in a new window
Map
Tilghman Island, MD

What's nearby

  • Tilghman Watermen’s Museum - 3 min drive - 2.1 km
  • St. Michaels Marina - 27 min drive - 31.1 km
  • Chesapeake Bay Maritime Museum - 27 min drive - 31.1 km
  • St. Michaels Winery - 28 min drive - 31.8 km
  • Saint Michaels Village - 29 min drive - 33.1 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
  • ‪Bridge 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 does it cost to stay at Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets?

As of 26 Mar 2026, prices found for a 1-night stay for 2 adults at Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets on 30 May 2026 start from AU$433, 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.
Learn moreOpens 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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

8/10 Good

Tracy D.

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Elizabeth K.

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
Verified

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
Verified

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

About the host

Hosted by Jennifer Brown

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback