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Tilghman Island Waterfront | Private Dock - Image 1
Tilghman Island Waterfront | Private Dock - Image 2
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Tilghman Island Waterfront | Private Dock - Image 5

Tilghman, Maryland

Tilghman Island Waterfront | Private Dock

4 bedrooms4 beds4 baths8 guests

Escape to the edge of the Chesapeake on Tilghman Island. This 4-bedroom, 4-bath waterfront retreat sleeps 8 with wide-open Bay views, a private dock and the kind of peaceful setting that makes it easy to slow down. Spend crisp mornings with coffee overlooking the water, bike around the island, fish or crab from the dock, then come home in time for sunset. Just a short drive from St. Michaels, it’s an effortless escape for family weekends, trips with friends and quiet days on the Eastern Shore.

Talbot County Licensure: STRN-25-16

Here, the Chesapeake is part of the experience from the moment you arrive.

Wide-open water views frame the home and set the pace for days spent a little more slowly. Start with coffee overlooking the Bay, wander down to the private dock, explore Tilghman Island by bike, or simply stay put and watch the boats pass by. Inside, the home comfortably welcomes up to 8 guests across 4 bedrooms and 4 bathrooms. The first-floor primary suite offers water views and easy main-level living, while three additional bedrooms upstairs give families and groups plenty of room to settle in.

WHAT YOU’LL LOVE

• Direct Chesapeake Bay waterfront
• Private dock for fishing + crabbing
• Wide-open water views
• 4 bedrooms + 4 bathrooms
• Sleeps up to 8 guests
• First-floor primary suite
• Walk to the community beach
• Indoor + outdoor dining
• BBQ grill
• Short drive to St. Michaels
• Private seasonal pool

Fall and winter bring their own kind of magic to Tilghman Island , quiet roads, crisp air, beautiful sunsets and the feeling that you have a little corner of the Chesapeake to yourself. Spend the day exploring St. Michaels or stay home and gather around the table. There’s no need to over-plan this one.

When warmer days return, the property transforms for summer with a private waterfront pool, expansive deck and days spent outside from morning until sunset. The pool is seasonal and scheduled to open by Memorial Day.

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.

Starter supply of paper towels, toilet paper, and basic toiletries provided.

Please bring extra supplies if you prefer more than the starter set.

Quiet, residential neighborhood — respect local noise guidelines.

The private pool is scheduled to open for the season by Memorial Day.

Property License: ST-557-LEE

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (excl. fees and taxes)AvailabilityMin Stay (nights)
Nov 13, 2026$499Not Available3
Nov 14, 2026$499Not Available3
Nov 15, 2026$499Not Available3
Nov 16, 2026$499Not Available3
Nov 17, 2026$499Not Available3
Nov 18, 2026$499Not Available3
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Dec 1, 2026$499Not Available3
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May 1, 2027$650Available3
May 2, 2027$650Available3
May 3, 2027$650Available3
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May 25, 2027$650Available3
May 26, 2027$650Available3
May 27, 2027$650Available3
May 28, 2027$895Available3
May 29, 2027$895Available3
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Jun 1, 2027$895Available3
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Jun 10, 2027$895Not Available3
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Jun 20, 2027$895Not Available7
Jun 21, 2027$895Available7
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Jun 26, 2027$895Available7
Jun 27, 2027$895Available7
Jun 28, 2027$895Available7
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Jun 30, 2027$895Not Available7
Jul 1, 2027$975Not Available7
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Sep 1, 2027$895Available3
Sep 2, 2027$895Available3
Sep 3, 2027$895Available3
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Sep 19, 2027$895Available3
Sep 20, 2027$625Available3
Sep 21, 2027$625Available3
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Sep 24, 2027$625Available3
Sep 25, 2027$625Available3
Sep 26, 2027$625Available3
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Sep 28, 2027$625Available3
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Oct 1, 2027$499Available3
Oct 2, 2027$499Available3
Oct 3, 2027$499Available3
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Nov 1, 2027$499Available3
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Dec 1, 2027$499Available3
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What this home offers

Pool outdoor
BBQ Area
Air conditioning
Bathtub
Bed linens

Where you’ll be

Tilghman, Maryland, 21671, United States

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Check-in & check-out

Check-in after 4:00 PM.

Check-out before 10:00 AM.

Property rules

Children welcome (2–12 years).

Infants welcome (under 2).

Maximum 8 guests.

No pets allowed.

No parties or events.

Cancellation policy

Add your trip dates to get the cancellation details for this stay.