# Waterfront Retreat | Near St. Michaels & Tilghman – 4 Bedroom Vacation Rental in Sherwood, Maryland | Flaneur, the vacation rental company

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 URL**: https://flaneur-the-vacation-rental-company.wanderos.com/property/731564004186522475/waterfront-retreat-near-st-michaels-tilghman
**Markdown URL**: https://flaneur-the-vacation-rental-company.wanderos.com/property/731564004186522475/waterfront-retreat-near-st-michaels-tilghman.md

## Property Overview
- **Sleeps**: 8 guests
- **Bedrooms**: 4 bedrooms
- **Bathrooms**: 3
- **Square Footage**: 1,000 sq ft

- **Property License**: STN-26-13

## Pricing & Availability
- **Nightly Rate**: $350 USD - $615 USD (before taxes and fees)
- **Next Available**: Nov 21, 2026
- **Available Days**: 517 of 551 days between Nov 13, 2026 and May 16, 2028
- **Daily Pricing (Nov 13, 2026 to May 16, 2028)**:
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  - Oct 4, 2027: $615 USD (Available) (3 night min)
  - Oct 5, 2027: $615 USD (Available) (3 night min)
  - Oct 6, 2027: $615 USD (Available) (3 night min)
  - Oct 7, 2027: $615 USD (Available) (3 night min)
  - Oct 8, 2027: $615 USD (Available) (3 night min)
  - Oct 9, 2027: $615 USD (Available) (3 night min)
  - Oct 10, 2027: $615 USD (Available) (3 night min)
  - Oct 11, 2027: $615 USD (Available) (3 night min)
  - Oct 12, 2027: $615 USD (Available) (3 night min)
  - Oct 13, 2027: $615 USD (Available) (3 night min)
  - Oct 14, 2027: $615 USD (Available) (3 night min)
  - Oct 15, 2027: $615 USD (Available) (3 night min)
  - Oct 16, 2027: $615 USD (Available) (3 night min)
  - Oct 17, 2027: $615 USD (Available) (3 night min)
  - Oct 18, 2027: $615 USD (Available) (3 night min)
  - Oct 19, 2027: $615 USD (Available) (3 night min)
  - Oct 20, 2027: $615 USD (Available) (3 night min)
  - Oct 21, 2027: $615 USD (Available) (3 night min)
  - Oct 22, 2027: $615 USD (Available) (3 night min)
  - Oct 23, 2027: $615 USD (Available) (3 night min)
  - Oct 24, 2027: $615 USD (Available) (3 night min)
  - Oct 25, 2027: $615 USD (Available) (3 night min)
  - Oct 26, 2027: $615 USD (Available) (3 night min)
  - Oct 27, 2027: $615 USD (Available) (3 night min)
  - Oct 28, 2027: $615 USD (Available) (3 night min)
  - Oct 29, 2027: $615 USD (Available) (3 night min)
  - Oct 30, 2027: $615 USD (Available) (3 night min)
  - Oct 31, 2027: $615 USD (Available) (3 night min)
  - Nov 1, 2027: $615 USD (Available) (3 night min)
  - Nov 2, 2027: $615 USD (Available) (3 night min)
  - Nov 3, 2027: $615 USD (Available) (3 night min)
  - Nov 4, 2027: $615 USD (Available) (3 night min)
  - Nov 5, 2027: $615 USD (Available) (3 night min)
  - Nov 6, 2027: $615 USD (Available) (3 night min)
  - Nov 7, 2027: $615 USD (Available) (3 night min)
  - Nov 8, 2027: $615 USD (Available) (3 night min)
  - Nov 9, 2027: $615 USD (Available) (3 night min)
  - Nov 10, 2027: $615 USD (Available) (3 night min)
  - Nov 11, 2027: $615 USD (Available) (3 night min)
  - Nov 12, 2027: $615 USD (Available) (3 night min)
  - Nov 13, 2027: $615 USD (Available) (3 night min)
  - Nov 14, 2027: $615 USD (Available) (3 night min)
  - Nov 15, 2027: $615 USD (Available) (3 night min)
  - Nov 16, 2027: $615 USD (Available) (3 night min)
  - Nov 17, 2027: $615 USD (Available) (3 night min)
  - Nov 18, 2027: $615 USD (Available) (3 night min)
  - Nov 19, 2027: $615 USD (Available) (3 night min)
  - Nov 20, 2027: $615 USD (Available) (3 night min)
  - Nov 21, 2027: $615 USD (Available) (3 night min)
  - Nov 22, 2027: $615 USD (Available) (3 night min)
  - Nov 23, 2027: $615 USD (Available) (3 night min)
  - Nov 24, 2027: $615 USD (Available) (3 night min)
  - Nov 25, 2027: $615 USD (Available) (3 night min)
  - Nov 26, 2027: $615 USD (Available) (3 night min)
  - Nov 27, 2027: $615 USD (Available) (3 night min)
  - Nov 28, 2027: $615 USD (Available) (3 night min)
  - Nov 29, 2027: $615 USD (Available) (3 night min)
  - Nov 30, 2027: $615 USD (Available) (3 night min)
  - Dec 1, 2027: $615 USD (Available) (3 night min)
  - Dec 2, 2027: $615 USD (Available) (3 night min)
  - Dec 3, 2027: $615 USD (Available) (3 night min)
  - Dec 4, 2027: $615 USD (Available) (3 night min)
  - Dec 5, 2027: $615 USD (Available) (3 night min)
  - Dec 6, 2027: $615 USD (Available) (3 night min)
  - Dec 7, 2027: $615 USD (Available) (3 night min)
  - Dec 8, 2027: $615 USD (Available) (3 night min)
  - Dec 9, 2027: $615 USD (Available) (3 night min)
  - Dec 10, 2027: $615 USD (Available) (3 night min)
  - Dec 11, 2027: $615 USD (Available) (3 night min)
  - Dec 12, 2027: $615 USD (Available) (3 night min)
  - Dec 13, 2027: $615 USD (Available) (3 night min)
  - Dec 14, 2027: $615 USD (Available) (3 night min)
  - Dec 15, 2027: $615 USD (Available) (3 night min)
  - Dec 16, 2027: $615 USD (Available) (3 night min)
  - Dec 17, 2027: $615 USD (Available) (3 night min)
  - Dec 18, 2027: $615 USD (Available) (3 night min)
  - Dec 19, 2027: $615 USD (Available) (3 night min)
  - Dec 20, 2027: $615 USD (Available) (3 night min)
  - Dec 21, 2027: $615 USD (Available) (3 night min)
  - Dec 22, 2027: $615 USD (Available) (3 night min)
  - Dec 23, 2027: $615 USD (Available) (3 night min)
  - Dec 24, 2027: $615 USD (Available) (3 night min)
  - Dec 25, 2027: $615 USD (Available) (3 night min)
  - Dec 26, 2027: $615 USD (Available) (3 night min)
  - Dec 27, 2027: $615 USD (Available) (3 night min)
  - Dec 28, 2027: $615 USD (Available) (3 night min)
  - Dec 29, 2027: $615 USD (Available) (3 night min)
  - Dec 30, 2027: $615 USD (Available) (3 night min)
  - Dec 31, 2027: $615 USD (Available) (3 night min)
  - Jan 1, 2028: $615 USD (Available) (3 night min)
  - Jan 2, 2028: $615 USD (Available) (3 night min)
  - Jan 3, 2028: $615 USD (Available) (3 night min)
  - Jan 4, 2028: $615 USD (Available) (3 night min)
  - Jan 5, 2028: $615 USD (Available) (3 night min)
  - Jan 6, 2028: $615 USD (Available) (3 night min)
  - Jan 7, 2028: $615 USD (Available) (3 night min)
  - Jan 8, 2028: $615 USD (Available) (3 night min)
  - Jan 9, 2028: $615 USD (Available) (3 night min)
  - Jan 10, 2028: $615 USD (Available) (3 night min)
  - Jan 11, 2028: $615 USD (Available) (3 night min)
  - Jan 12, 2028: $615 USD (Available) (3 night min)
  - Jan 13, 2028: $615 USD (Available) (3 night min)
  - Jan 14, 2028: $615 USD (Available) (3 night min)
  - Jan 15, 2028: $615 USD (Available) (3 night min)
  - Jan 16, 2028: $615 USD (Available) (3 night min)
  - Jan 17, 2028: $615 USD (Available) (3 night min)
  - Jan 18, 2028: $615 USD (Available) (3 night min)
  - Jan 19, 2028: $615 USD (Available) (3 night min)
  - Jan 20, 2028: $615 USD (Available) (3 night min)
  - Jan 21, 2028: $615 USD (Available) (3 night min)
  - Jan 22, 2028: $615 USD (Available) (3 night min)
  - Jan 23, 2028: $615 USD (Available) (3 night min)
  - Jan 24, 2028: $615 USD (Available) (3 night min)
  - Jan 25, 2028: $615 USD (Available) (3 night min)
  - Jan 26, 2028: $615 USD (Available) (3 night min)
  - Jan 27, 2028: $615 USD (Available) (3 night min)
  - Jan 28, 2028: $615 USD (Available) (3 night min)
  - Jan 29, 2028: $615 USD (Available) (3 night min)
  - Jan 30, 2028: $615 USD (Available) (3 night min)
  - Jan 31, 2028: $615 USD (Available) (3 night min)
  - Feb 1, 2028: $615 USD (Available) (3 night min)
  - Feb 2, 2028: $615 USD (Available) (3 night min)
  - Feb 3, 2028: $615 USD (Available) (3 night min)
  - Feb 4, 2028: $615 USD (Available) (3 night min)
  - Feb 5, 2028: $615 USD (Available) (3 night min)
  - Feb 6, 2028: $615 USD (Available) (3 night min)
  - Feb 7, 2028: $615 USD (Available) (3 night min)
  - Feb 8, 2028: $615 USD (Available) (3 night min)
  - Feb 9, 2028: $615 USD (Available) (3 night min)
  - Feb 10, 2028: $615 USD (Available) (3 night min)
  - Feb 11, 2028: $615 USD (Available) (3 night min)
  - Feb 12, 2028: $615 USD (Available) (3 night min)
  - Feb 13, 2028: $615 USD (Available) (3 night min)
  - Feb 14, 2028: $615 USD (Available) (3 night min)
  - Feb 15, 2028: $615 USD (Available) (3 night min)
  - Feb 16, 2028: $615 USD (Available) (3 night min)
  - Feb 17, 2028: $615 USD (Available) (3 night min)
  - Feb 18, 2028: $615 USD (Available) (3 night min)
  - Feb 19, 2028: $615 USD (Available) (3 night min)
  - Feb 20, 2028: $615 USD (Available) (3 night min)
  - Feb 21, 2028: $615 USD (Available) (3 night min)
  - Feb 22, 2028: $615 USD (Available) (3 night min)
  - Feb 23, 2028: $615 USD (Available) (3 night min)
  - Feb 24, 2028: $615 USD (Available) (3 night min)
  - Feb 25, 2028: $615 USD (Available) (3 night min)
  - Feb 26, 2028: $615 USD (Available) (3 night min)
  - Feb 27, 2028: $615 USD (Available) (3 night min)
  - Feb 28, 2028: $615 USD (Available) (3 night min)
  - Feb 29, 2028: $615 USD (Available) (3 night min)
  - Mar 1, 2028: $615 USD (Available) (3 night min)
  - Mar 2, 2028: $615 USD (Available) (3 night min)
  - Mar 3, 2028: $615 USD (Available) (3 night min)
  - Mar 4, 2028: $615 USD (Available) (3 night min)
  - Mar 5, 2028: $615 USD (Available) (3 night min)
  - Mar 6, 2028: $615 USD (Available) (3 night min)
  - Mar 7, 2028: $615 USD (Available) (3 night min)
  - Mar 8, 2028: $615 USD (Available) (3 night min)
  - Mar 9, 2028: $615 USD (Available) (3 night min)
  - Mar 10, 2028: $615 USD (Available) (3 night min)
  - Mar 11, 2028: $615 USD (Available) (3 night min)
  - Mar 12, 2028: $615 USD (Available) (3 night min)
  - Mar 13, 2028: $615 USD (Available) (3 night min)
  - Mar 14, 2028: $615 USD (Available) (3 night min)
  - Mar 15, 2028: $615 USD (Available) (3 night min)
  - Mar 16, 2028: $615 USD (Available) (3 night min)
  - Mar 17, 2028: $615 USD (Available) (3 night min)
  - Mar 18, 2028: $615 USD (Available) (3 night min)
  - Mar 19, 2028: $615 USD (Available) (3 night min)
  - Mar 20, 2028: $615 USD (Available) (3 night min)
  - Mar 21, 2028: $615 USD (Available) (3 night min)
  - Mar 22, 2028: $615 USD (Available) (3 night min)
  - Mar 23, 2028: $615 USD (Available) (3 night min)
  - Mar 24, 2028: $615 USD (Available) (3 night min)
  - Mar 25, 2028: $615 USD (Available) (3 night min)
  - Mar 26, 2028: $615 USD (Available) (3 night min)
  - Mar 27, 2028: $615 USD (Available) (3 night min)
  - Mar 28, 2028: $615 USD (Available) (3 night min)
  - Mar 29, 2028: $615 USD (Available) (3 night min)
  - Mar 30, 2028: $615 USD (Available) (3 night min)
  - Mar 31, 2028: $615 USD (Available) (3 night min)
  - Apr 1, 2028: $615 USD (Available) (3 night min)
  - Apr 2, 2028: $615 USD (Available) (3 night min)
  - Apr 3, 2028: $615 USD (Available) (3 night min)
  - Apr 4, 2028: $615 USD (Available) (3 night min)
  - Apr 5, 2028: $615 USD (Available) (3 night min)
  - Apr 6, 2028: $615 USD (Available) (3 night min)
  - Apr 7, 2028: $615 USD (Available) (3 night min)
  - Apr 8, 2028: $615 USD (Available) (3 night min)
  - Apr 9, 2028: $615 USD (Available) (3 night min)
  - Apr 10, 2028: $615 USD (Available) (3 night min)
  - Apr 11, 2028: $615 USD (Available) (3 night min)
  - Apr 12, 2028: $615 USD (Available) (3 night min)
  - Apr 13, 2028: $615 USD (Available) (3 night min)
  - Apr 14, 2028: $615 USD (Available) (3 night min)
  - Apr 15, 2028: $615 USD (Available) (3 night min)
  - Apr 16, 2028: $615 USD (Available) (3 night min)
  - Apr 17, 2028: $615 USD (Available) (3 night min)
  - Apr 18, 2028: $615 USD (Available) (3 night min)
  - Apr 19, 2028: $615 USD (Available) (3 night min)
  - Apr 20, 2028: $615 USD (Available) (3 night min)
  - Apr 21, 2028: $615 USD (Available) (3 night min)
  - Apr 22, 2028: $615 USD (Available) (3 night min)
  - Apr 23, 2028: $615 USD (Available) (3 night min)
  - Apr 24, 2028: $615 USD (Available) (3 night min)
  - Apr 25, 2028: $615 USD (Available) (3 night min)
  - Apr 26, 2028: $615 USD (Available) (3 night min)
  - Apr 27, 2028: $615 USD (Available) (3 night min)
  - Apr 28, 2028: $615 USD (Available) (3 night min)
  - Apr 29, 2028: $615 USD (Available) (3 night min)
  - Apr 30, 2028: $615 USD (Available) (3 night min)
  - May 1, 2028: $615 USD (Available) (3 night min)
  - May 2, 2028: $615 USD (Available) (3 night min)
  - May 3, 2028: $615 USD (Available) (3 night min)
  - May 4, 2028: $615 USD (Available) (3 night min)
  - May 5, 2028: $615 USD (Available) (3 night min)
  - May 6, 2028: $615 USD (Available) (3 night min)
  - May 7, 2028: $615 USD (Available) (3 night min)
  - May 8, 2028: $615 USD (Available) (3 night min)
  - May 9, 2028: $615 USD (Available) (3 night min)
  - May 10, 2028: $615 USD (Available) (3 night min)
  - May 11, 2028: $615 USD (Available) (3 night min)
  - May 12, 2028: $615 USD (Available) (3 night min)
  - May 13, 2028: $615 USD (Available) (3 night min)
  - May 14, 2028: $615 USD (Available) (3 night min)
  - May 15, 2028: $615 USD (Available) (3 night min)
  - May 16, 2028: $615 USD (Available) (3 night min)


## Availability Rules 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 listed minimum stay, and no intervening nights are marked "Not Available".
- Prices are nightly rates before taxes and fees. Final checkout pricing may include taxes, fees, add-ons, discounts, and payment terms.
- The daily pricing table covers every date through May 16, 2028. A date missing from the table has no published nightly rate.
- If a requested date range extends beyond the table, visit the property URL for live booking details.

## Stay Timing
- **Check-in**: After 4:00 PM
- **Check-out**: Before 10:00 AM

## Location
- **Address**: Sherwood, Maryland, United States
- **Postal Code**: 21665
- **Coordinates**: 38.7701051, -76.3185131
- **Local Area**: Beautiful destination with local attractions

## Amenities
- Pool outdoor
- Air conditioning
- Bed linens
- Coffee maker
- Cooking basics
- Dishes
- Dishwasher
- Dryer
- Toys
- Free parking
- Hair dryer
- Heating
- Wifi
- Iron
- Kitchen
- Microwave
- Oven
- Fridge
- Smoke detector
- Stove
- TV
- Washer



## Guest Services
- **24/7 Concierge**: Available through the Flaneur, the vacation rental company app
- **Housekeeping**: Professional cleaning service
- **Maintenance**: On-call support for any issues
- **Local Recommendations**: Dining, activities, and experiences

## Property Details
- **Property ID**: 731564004186522475
- **Property Slug**: waterfront-retreat-near-st-michaels-tilghman

## Booking Information
For more information and to book this property, visit:
https://flaneur-the-vacation-rental-company.wanderos.com/property/731564004186522475/waterfront-retreat-near-st-michaels-tilghman

Or contact Flaneur, the vacation rental company customer service for assistance.

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*Last modified: Nov 13, 2026*
*This markdown file is generated automatically for AI agents and search engines.*
