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Sherwood, Maryland

Waterfront Retreat | Near St. Michaels & Tilghman

4 bedrooms5 beds3 baths8 guests

A completely reimagined waterfront retreat between St. Michaels and Tilghman Island. Made for long summer days by the pool, crisp mornings by the water, and cozy Eastern Shore weekends with the people you love.

This beautifully remodeled 4-bedroom home brings together everything we love about a stay on the Shore: water just outside your door, beautiful spaces to gather, a private seasonal pool, and easy access to both St. Michaels and Tilghman Island.

Come for the water. Stay for the slower mornings, dinner around the table, and the kind of weekends you wish lasted a little longer.

Talbot County Licensure: STN-26-13

Every season feels a little different on the Eastern Shore and we happen to think the quieter months are some of the best. Fall brings crisp mornings, changing leaves and afternoons made for wandering through St. Michaels. Winter slows everything down even further. The towns are quieter, the water is peaceful, and suddenly a weekend with nowhere you need to be feels like exactly what you needed.

This completely remodeled 4-bedroom waterfront home was thoughtfully reimagined for those moments.
Start the morning slowly with coffee and a view of the water. Spend the afternoon exploring the shops and restaurants of St. Michaels, take the scenic drive toward Tilghman Island, or simply stay put and enjoy the quiet. Then come home, pour a glass of wine, make dinner together and settle in for the evening.

Inside, fresh interiors and comfortable gathering spaces create a home that feels elevated without losing the warmth you want from a weekend away. There’s room to spread out when you want it and plenty of space to come together when you don’t. Outside, the waterfront setting is the backdrop year-round. During warmer months, days naturally revolve around the private seasonal pool and time spent outdoors. As the weather cools, the experience changes, quiet mornings by the water, bundled-up walks, golden sunsets and evenings spent back inside with your favorite people.

WHAT YOU’LL LOVE

• Waterfront setting with beautiful views
• Beautiful spaces for cooking, dining and gathering
• Private seasonal pool
• Close to downtown St. Michaels and Tilghman Island
• Peaceful setting for fall and winter escapes
• Perfect for couples’ weekends, family getaways and holiday stays

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

Property License: STN-26-13

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$615Not Available3
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Nov 21, 2026$350Available3
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What this home offers

Pool outdoor
Air conditioning
Bed linens
Coffee maker
Cooking basics

Where you’ll be

Sherwood, Maryland, 21665, 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.