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Waterfront Retreat | Near St. Michaels & Tilghman

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A modern kitchen with dark blue cabinets, stainless steel appliances, and a central island. - Waterfront Retreat | Near St. Michaels & Tilghman (Sherwood)
A sunroom with a sectional sofa, a coffee table, and a view of a forest through large windows. - Waterfront Retreat | Near St. Michaels & Tilghman (Sherwood)
A two-story house with a front porch, multiple windows, and a visible front door. - Waterfront Retreat | Near St. Michaels & Tilghman (Sherwood)
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a view of a body of water. - Waterfront Retreat | Near St. Michaels & Tilghman (Sherwood)
A bedroom with a large bed, two bedside tables, a rug, and windows with a view of trees. - Waterfront Retreat | Near St. Michaels & Tilghman (Sherwood)
Waterfront Retreat | Near St. Michaels & Tilghman provides everything that you need. Stay connected with in-room WiFi.

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Parking available
  • Water view

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About this property

Waterfront Retreat | Near St. Michaels & Tilghman

  • Summary:

    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



    The Space:

    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.



    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.



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



    Interaction with Guests:

    Nanny Goat is situated on a beautiful 24-acre property with several other buildings located throughout the grounds. Your home and designated outdoor spaces are private, and we simply ask that guests remain within the Nanny Goat boundaries during their stay. Fencing, plantings and signage throughout the property make these areas easy to identify.



    The property is professionally maintained each week, so you may occasionally see our grounds or property care team tending to the larger property during your stay.



    A few of the other buildings on the 24-acre property are also currently undergoing renovations, so there may occasionally be contractors working elsewhere on the grounds. We do our best to ensure this does not interfere with your stay or the privacy of Nanny Goat, but wanted to share this upfront so there are no surprises.



    Even with the activity elsewhere on the property, Nanny Goat remains a wonderfully private retreat with plenty of space to settle in, enjoy the waterfront and make the property feel like your own while you're here.

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • TV

Laundry

  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the waterfront

Things to do

  • Optional golf privileges

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)
  • First aid kit
  • Fire extinguisher

Policies

Check-in

Check-in time starts at 4:00 PM

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 not allowed

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
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 and a first aid kit
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

About the area

Located in Sherwood, 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 landmarks include St. Michaels Museum and Captain Avery Museum. Visit our Sherwood travel guide
View more Holiday homes in Sherwood
Map
Sherwood, MD

What's nearby

  • A large suspension bridge over a calm body of water with a sunset in the background.
    Northern Chesapeake Bay
    7 min drive - 8.2 km
  • Knapp's Narrows Marina & Inn
    6 min drive - 6.8 km
  • Back Creek Community Park
    6 min drive - 6.8 km
  • Tilghman Island Marina
    7 min drive - 8.2 km
  • Tilghman Watermen’s Museum
    7 min drive - 8.9 km

Getting around

  • Easton, MD (ESN-Easton - Newnam)
    38 min drive

Restaurants

  • Foxy's Harbor Grille
    16 min drive
  • The Crab Claw
    15 min drive
  • Chesapeake Landing
    10 min drive
  • Talbot St. Tavern
    15 min drive
  • Purser's Pub
    14 min drive

Frequently asked questions

Is Waterfront Retreat | Near St. Michaels & Tilghman pet-friendly?

No, pets are not allowed at this property.

How much is parking at Waterfront Retreat | Near St. Michaels & Tilghman?

On-site parking is available at the property.

What time is check-in at Waterfront Retreat | Near St. Michaels & Tilghman?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront Retreat | Near St. Michaels & Tilghman?

Checkout is at 10:00 AM.

Where is Waterfront Retreat | Near St. Michaels & Tilghman located?

Situated on the waterfront, this holiday home is 2.7 mi (4.3 km) from Goat Island and 2.9 mi (4.6 km) from Wittman Park. Back Creek Community Park and Knapp's Narrows Marina & Inn are also within 6 miles (10 km).

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