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Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
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Reviews
10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms2+ bathroomsSleeps 6
Popular amenities
Explore the area

Tilghman Island, MD
- Place, Tilghman Watermen’s Museum3 min drive
- Place, Chesapeake Bay Maritime Museum27 min drive
- Place, St. Michaels Winery28 min drive
- Airport, Easton, MD (ESN-Easton - Newnam)46 min drive
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.
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
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Outdoor space
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10.0 out of 10, Exceptional, (43 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets 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
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.

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
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
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
Verified
19 September 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Sep 2025
Verified
10/10 Excellent
Jane M.
14 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Jane M.
Stayed 3 nights in Jul 2025
Verified
10/10 Excellent
Karolyn J.
18 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing Getaway
Karolyn J.
Stayed 3 nights in May 2025
Verified
10/10 Excellent
Rhonda G.
6 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Vacation
Rhonda G.
Stayed 4 nights in Aug 2024
Verified
10/10 Excellent
Gary B.
6 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
An excellent vacation rental
Gary B.
Stayed 3 nights in Jun 2025
Verified
10/10 Excellent
Olivia J.
26 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful little oasis!
Olivia J.
Stayed 3 nights in Jun 2024
Verified
10/10 Excellent
Stephanie E.
12 October 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy



Stephanie E.
Stayed 6 nights in Oct 2025
Verified
10/10 Excellent
Kim D.
13 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Waterfront Property
Kim D.
Stayed 3 nights in Aug 2024
Verified
8/10 Good
Tracy D.
5 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, peaceful home
Tracy D.
Stayed 3 nights in Jun 2023
Verified
10/10 Excellent
Bradley N.
17 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Place!
Bradley N.
Stayed 3 nights in Jul 2024
Verified
10/10 Excellent
Kelly K.
17 October 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Time
Kelly K.
Stayed 3 nights in Oct 2022
Verified
10/10 Excellent
Brian D.
17 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay for a long weekend
Brian D.
Stayed 3 nights in Jul 2023
Verified
10/10 Excellent
MaryBeth G.
30 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Anniversary weekend
MaryBeth G.
Stayed 3 nights in Oct 2024
Verified
10/10 Excellent
ashley m.
25 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Girls trip
ashley m.
Stayed 3 nights in Jul 2023
Verified
10/10 Excellent
MaryBeth G.
15 November 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Yearly anniversary weekend to area
MaryBeth G.
Stayed 3 nights in Nov 2023
Verified
10/10 Excellent
Berta K.
6 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Bay Views
Berta K.
Stayed 4 nights in Jul 2023
Verified
10/10 Excellent
Heather T.
24 March 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful!
Heather T.
Stayed 5 nights in Mar 2023
Verified
8/10 Good
Carol S.
3 April 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful spot
Carol S.
Stayed 3 nights in Mar 2023
Verified
10/10 Excellent
Donna C.
19 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic!
Donna C.
Stayed 3 nights in Jul 2024
Verified
10/10 Excellent
Kevin J.
20 October 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved “The Waterman”
Kevin J.
Stayed 3 nights in Oct 2022
Verified
10/10 Excellent
Rhonda R.
16 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Unbelievable view
Rhonda R.
Stayed 3 nights in Jun 2023
Verified
10/10 Excellent
Jan K.
6 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
This house and location are beyond beautiful!
Jan K.
Stayed 3 nights in Oct 2024
Verified
10/10 Excellent
Elizabeth K.
13 April 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet Getaway Retreat
Elizabeth K.
Stayed 3 nights in Apr 2023
Verified
10/10 Excellent
Marie B.
15 May 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Can I buy this property???
Marie B.
Stayed 6 nights in May 2023
Verified
10/10 Excellent
Joe F.
10 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peace and Quiet
Joe F.
Stayed 4 nights in Sep 2024
About the host
Hosted by Jennifer Brown
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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