Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Photo gallery for Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

A hallway leading to a living area with a fireplace, a television, and a dining area.
Property video
A dining area with wooden furniture, a ceiling fan, and a view of the outdoors.
A staircase with black and white steps leading to a second floor, a wooden door with glass panels, and a view of the outdoors through a window.
A kitchen with wooden cabinets, a central island with bar stools, a stove, and a view of the outdoors through large windows.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Pickleball on-site
    A rare find — enjoy pickleball without leaving the property.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
4 bedrooms2 bathroomsSleeps 14

Popular amenities

  • Private pool
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Taylors Island, MD
  • Place, Blackwater National Wildlife Refuge
    ‪11 min drive‬
  • Place, Long Wharf Park
    ‪38 min drive‬
  • Place, Gerry Boyle Park at Great Marsh
    ‪40 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪74 min drive‬

Rooms & beds

4 bedrooms (sleeps 14)

Bedroom 1

1 Double Futon and 1 King Bed

Bedroom 2

1 Double Futon and 1 Queen Bed

Bedroom 3

1 Double Bed

Bedroom 4

2 Single Beds

Loft

2 Double Beds and 1 Double Futon

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden
Dining area

About this property

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Beautifully appointed 19th century farmhouse situated on 23 acres of pristine beauty with pool and 2,000 feet of unspoiled shoreline located on the Chesapeake Bay of Maryland’s Eastern Shore. This waterfront property is perfect for family retreats, celebrations or a relaxing getaway. Take a step-back in time and enjoy the raw, natural surroundings of this idyllic and secluded setting. Enjoy the tranquil beauty of this agricultural farm and picturesque views. You’ll find an abundance of wildlife in their natural habitats throughout the property. For the sport enthusiast, enjoy fishing, crabbing, boating, and kayaking all in your own back yard and on your own private pier. Bring your boat or rent one to explore nearby islands and experience some of the best fishing and crabbing that the Chesapeake Bay has to offer. Charter fishing and guided hunting excursions are also locally available. Explore the shoreline and coves on the property for Indian artifacts, shells and sea glass. Taylors Island is bike friendly, so bring your bikes or rent them and ride to Palm Beach Willies for lunch or just explore all the natural beauty that the island has to offer.

Inside, you’ll find a fully equipped kitchen/great room with dual-sided wood-burning fireplace and wall-to-wall windows offering expansive views of the ample wildlife, sunsets and pristine Chesapeake Bay. A center island and farm table (combined seats 16) are perfect for family affairs. A screened-in patio is ideal for crab feasts and prime for entertaining with gas grill and exterior wood-burning fireplace. Enjoy an evening relaxing, roasting marshmallows and making smores. STARLINK Satellite internet available with WIFI speeds well in excess of 100 MBS with full streaming capabilities.

Gracious accommodations will greet you throughout with a spacious first floor queen bedroom with ornamental fireplace and pull-out sofa. The 2nd floor offers a king bedroom with ornamental fireplace and sofa bed; 1 double; 1 twin w/ trundle; and a loft with two double beds, and one day bed. Children's pack-n-play available.

Amenities: pier, pool, interior wood burning fireplace, exterior wood burning fireplace, central air, TV, DVD player, Bluetooth accessible indoor/outdoor stereo, fully equipped kitchen, microwave, air fryer, dishwasher, two refrigerators, 2 ice makers, washer & dryer, gas grill, three kayaks (1 two-person kayak, 1 one-person kayak, and 1 ocean kayak/Stand-Up Paddleboard), ping pong, foosball, grass volleyball court, outdoor basketball court, bocce ball, games, books, and video library.

For video of property please see.
https://youtube.com/shorts/BhppOwT3YVQ?feature=share

If you have a party larger than this home will accommodate or just want more space, we offer a second home on the island approximately 1/2 mile away that can sleep up to 6 additional guests called the Taylors Island Bunkhouse. For a short video showing this property use this link:
https://youtu.be/58JAcRs5OhM

Home and property is available for large events such as weddings with prior owner approval, subject to certain conditions and additional fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 35
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
Games provided and activities for all ages
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Events

Events allowed
Weddings and large functions req. add fee etc.
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Return any and all recreational items to their original locations. make sure umbrellas are down and secured at pool.
Notify owners of any issues, broken items, or concerns. please ensure storm door is engaged at front door.
Set thermostats to 82 degrees (Summer)or 52 degrees in the winter months
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property # 120352vb
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
Parties and events are allowed on site
Note from host: weddings and large functions req. add fee etc.
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, a first aid kit and a deadlock

About the area

Taylors Island

Located in Taylors Island, this holiday home is in a rural area and on the waterfront. Harriet Tubman Underground Railroad National Historical Park and Cove Point Lighthouse are local landmarks, and some of the area's activities can be experienced at Flag Harbor Marina and Chesapeake Hills Golf Course. Discover the area's water adventures with kayaking and waterskiing nearby, or enjoy the great outdoors with hunting and cycling.
Map
Taylors Island, MD

What's nearby

  • Blackwater National Wildlife Refuge - 11 min drive - 9.4 km
  • Harriet Tubman Museum and Educational Center - 37 min drive - 39.9 km
  • Long Wharf Park - 38 min drive - 40.6 km
  • Choptank River Lighthouse - 38 min drive - 40.6 km
  • Gerry Boyle Park at Great Marsh - 40 min drive - 41.6 km

Getting around

  • Cambridge Station - 40 min drive
  • Easton, MD (ESN-Easton - Newnam) - 62 min drive

Restaurants

  • ‪Soft & Salty Seafood - ‬61 min drive
  • ‪Millie's at Madison Bay - ‬20 min drive

Frequently asked questions

Does Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball?

As of 25 Aug, 2026, prices found for a 1-night stay for 2 adults at Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball on 22 Oct, 2026 start from S$2,920, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball pet-friendly?

No, pets are not allowed at this property.

How much is parking at Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball?

On-site parking is available at the property.

What time is check-in at Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball?

Check-in begins at 4:00 PM.

What time is check-out at Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball?

Checkout is at 10:00 AM.

Where is Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball located?

This family-friendly Taylors Island holiday home is located on the waterfront, 4.6 mi (7.4 km) from Blackwater National Wildlife Refuge, and within 20 mi (32 km) of Pot Island and Gunners Island. Christ Rock Park and Snows Turn Park are also within 20 miles (32 km).

About the host

Hosted by Ned Howe

Host profile image
I develop real estate for a living and have 3 children that have been able to experience the true meaning of Chesapeake Life.

Why they chose this property

Always enjoyed the Chesapeake Bay and all it had to offer and wanted a place to truly embellish my passion. This home hearkens back to a past few understand, as Taylor's Island has remained the same for hundreds of years. The home is not set directly on the water and allows you to view how wildlife exists within the zone of land that is along the water but is not disturbed by man made structures.

What makes this property unique

You can live with nature in unspoiled natural surroundings. Your only neighbors have 4 legs, wings or fins. If you are looking for a secluded location that offers tremendous beauty and access to all that the Chesapeake Bay offers then Taylor's Island is your spot and this fully restored telescoping home that was originally constructed in the 1700's is your sanctuary.

Languages:

English

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