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Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

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Property grounds
Dining
3 bedrooms, iron/ironing board, WiFi, bed sheets
Interior
TV, offices

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

Similar properties

Outdoor banquet area
The Tilghman Island Inn
Tilghman
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
4.8 out of 5, Exceptional, 135 reviews
$255 nightly
The price is $281
Jun 29 - Jun 30
Total with taxes and fees
The Tilghman Island Inn

About the neighborhood

Tilghman

When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay. .This vacation home is 1.1 mi (1.8 km) from Tilghman Watermen’s Museum and 1.3 mi (2.2 km) from Talbot County Library Tilghman Branch.
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

  • ‪Two if by Sea - ‬3 min drive
  • ‪Big Mack's Kitchen & Dock Bar - ‬4 min drive
  • ‪Marker Five Waterfront Dining - ‬4 min drive
  • ‪Gina’s @ The Bridge - ‬4 min drive
  • ‪Tickler's Crab Shack and Restaurant - ‬3 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.
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Conveniences include a microwave and a coffee/tea maker.
Take in the views from a garden and make use of amenities such as barbecue grills.
Guests will find features like internet access, onsite parking, and a car charging station.

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 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
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

Property is also known as

62c2daf68de6ff0035da2b31

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 38 out of 41 reviews
Rating 8 - Good. 3 out of 41 reviews
Rating 6 - Okay. 0 out of 41 reviews
Rating 4 - Poor. 0 out of 41 reviews
Rating 2 - Terrible. 0 out of 41 reviews

9.8/10

Cleanliness

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Austin D.

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

Gorgeous waterfront house

This house was pretty spectacular. Super clean and well appointed. Beautiful kitchen and amazing wraparound view of the water. The view really is amazing. Jennifer Brown, the property manager was also AMAZING. She was so nice and responsive and even offered to get us groceries to have at the house prior to our stay. 100% recommend this house and working with Jennifer!
Stayed 3 nights in Jun 2023