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Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman vacation home with kitchen

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

A lakeside seating area with a fire pit, two Adirondack chairs, and a dock extending into the water.
A bedroom with a large window overlooking a body of water.
A view from a room with a sliding glass door to a deck overlooking a body of water, with a chair and a table visible.
A living room with a dark blue sofa, a wooden staircase, and a patterned rug.
A dining area with a wooden table, wicker chairs, a white lamp, and a chandelier.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms3 bathrooms

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Tilghman Island, MD
  • Place, Tilghman Watermen’s Museum
    ‪4 min drive‬
  • Place, Chesapeake Bay Maritime Museum
    ‪28 min drive‬
  • Place, St. Michaels Winery
    ‪29 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪49 min drive‬

Room options

About the neighborhood

Tilghman

On river.Within a 15-minute walk of the vacation home, you'll find Chesapeake Bay and Northern Chesapeake Bay. Tilghman Watermen’s Museum and Talbot County Library Tilghman Branch are also within 2 miles (3 km).
View more Vacation Homes in TilghmanOpens in a new window

What's nearby

  • Tilghman Watermen’s Museum - 4 min drive - 2.0 miles
  • St. Michaels Marina - 28 min drive - 20.0 miles
  • Chesapeake Bay Maritime Museum - 28 min drive - 20.0 miles
  • St. Michaels Winery - 29 min drive - 20.4 miles
  • Saint Michaels Village - 30 min drive - 21.3 miles

Getting around

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

Restaurants

  • ‪Big Mack's Kitchen & Dock Bar - ‬4 min drive
  • ‪Gina’s @ The Bridge - ‬4 min drive
  • ‪Tickler's Crab Shack and Restaurant - ‬3 min drive
  • ‪Two if by Sea - ‬3 min drive
  • ‪Marker Five Waterfront Dining - ‬4 min drive

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.

Similar properties

Exterior
Wylder Tilghman Island
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  • On private beach
  • Pool
  • Breakfast included
  • Pet friendly
4.5 out of 5, Wonderful, 114 reviews
$218 nightly
The price is $240
Sep 22 - Sep 23
Total with taxes and fees
Wylder Tilghman Island

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Electric car charging station on site
  • Parking on site

Kitchen

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

  • Smoking not allowed

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

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 welcome
  • Service animals 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. This property accepts cash. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Property is also known as

62c2daf68de6ff0035da2b31

Frequently asked questions

How close is Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets to the airport?

This vacation home is 26.9 mi (44-min drive) away from the Easton, MD (ESN-Easton - Newnam) airport, the closest popular airport to the property.

Does Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets?

No, there is no casino at this vacation home.

What time is check-in at Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets?

Check-in begins at 4:00 PM.

Is there free parking at Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets?

Free parking is not available at this vacation home.

Does Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets have a pool?

This vacation home does not have a pool.

Does Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets have a spa?

There are no spa services available at this vacation home.

How close is Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets to downtown Tilghman?

This vacation home is 0.4 mi away from Tilghman.

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 43 out of 47 reviews
Rating 8 - Good. 4 out of 47 reviews
Rating 6 - Okay. 0 out of 47 reviews
Rating 4 - Poor. 0 out of 47 reviews
Rating 2 - Terrible. 0 out of 47 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Pierce S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Will stay again when in town!
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Joe F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home in a beautiful location. We are repeat visitors and plan to visit again.
Stayed 4 nights in May 2026
Verified review

8/10 Good

Laura M.

Liked: Cleanliness, check-in, location
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!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Steph R.

Liked: Location
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.
Stayed 4 nights in Apr 2026
Verified review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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

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