Top 10% of guest reviews in this areaTop 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
Explore the area
Taylors Island, MD
Blackwater National Wildlife Refuge
Place, Blackwater National Wildlife Refuge
11 min drive
Long Wharf Park
Place, Long Wharf Park
38 min drive
Gerry Boyle Park at Great Marsh
Place, Gerry Boyle Park at Great Marsh
40 min drive
Easton, MD (ESN-Easton - Newnam)
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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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 hiking/biking trails and hunting.
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
Boats & Hose - 11 min drive
Madison Bay - 20 min drive
Soft & Salty Seafood - 61 min drive
Willey's Seafood - 11 min drive
Hershey Grill
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 1 August 2026, prices found for a 1-night stay for 2 adults at Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball on 6 January 2027 start from NZ$3,829, 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).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The Eastern Shore Bay house was great for our family—plenty of room, our kids loved the ladder to the loft with the foosball table and the chalkboard, and we all loved crabbing and fishing from the dock and in the adjacent coves. The view out to the water during family meals was stunning. We experienced some heavy storms during our stay and Ned was extremely responsive and helpful with organizing the yard cleanup. He even provided many crabbing tips that made our efforts much more productive than they would have been otherwise! All in all a very special place that we are glad we got to visit.
TJ S.
Stayed 6 nights in Jul 2026
Response from VrboOwner on 13 July 2026
Those are some gourmet looking soft crabs. You have now discovered the hidden treasure in our back yard. Please come back and do it again next year!
Three generations of our family stayed together there and really enjoyed kayaking, the pool and crabbing and eating seafood and veggies from Emily’s farm stand together. Visit to Harriet Tubman museum and Blackwater refuge were great too. Wonderful wildlife viewing at the property.
Lisa S.
Stayed 4 nights in Jun 2025
Response from VrboOwner on 2 July 2025
Glad you enjoyed your stay. Please come back again.
Great host, he answered all of our questions and was always available. Amazing property. It was huge and had so many activities. The kids loved the pool. We had an amazing time. Would recommend to everyone.
Family vacation was great. We spent a lot of time at the pier crabbing or in the pool. Only down fall was the mosquitos. Made it hard to enjoy outdoor activities.
Kim N.
Stayed 6 nights in Jul 2025
Response from VrboOwner on 29 July 2025
Glad you enjoyed your stay and sorry to hear that the mosquitos didn't cooperate. They can be irrelevant and they can sometimes be problematic depending on the weather (rain is the biggest factor) The property is treated weekly so they shouldn't ever get out of hand but definitely recommend some repellant for those times that they are more active.
We thoroughly enjoyed our first visit to the Chesapeake Bay Area. There were so many things to do on site we rarely left. Extended family enjoyed kayaking, exploring the cove, searching the mud flats, exploring the point, the various provided sports activities, and the pool.
Thomas S.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 20 August 2024
Thanks Thomas. Glad you enjoyed all the amenities.
Ned was an excellent host and easy to communicate with. The property was wonderful for a family gathering with great outdoor amenities and so much space. The main original house had charm with lovely fireplaces and possibly original floors. The kitchen had all the modern appliances needed. The location is remote so best to bring food with you. We’d definitely consider staying again. The views from the dock and the firepit were beautiful.
The property was perfect for a family vacation for anyone that doesn’t want to have to leave for other attractions. We had family from Grandma, parents and teens down to babies and literally everyone enjoyed full days of activities. Swimming, kayaking and family kickball games were the highlights of our stay.
Had a great time with family and friends in this well appointed historic home with all the modern comforts and conveniences. Ned, the homeowner, was super accommodating and answered all our questions during our stay. Definitely recommend and will rent in the future!
My family of 10 had a great time at this property. We loved the access to water and boats, as well as the (smallish) pool near the house. The kitchen was spacious, and the outdoor screened room was one of our favorite spots. The owner was very responsive and helpful when I asked questions. Would recommend.
We had a great time spotting wildlife- egrets fishing in the cove, white tail and Zika deer, wild turkeys and a bald eagle soaring over head while we played in the pool. The house was large with plenty of space to find alone time or all join together in the great room for fun and games. We had a great meal at Old Saltys on Hooper Island
Leisa M.
Stayed 7 nights in Jul 2022
Response from VrboOwner on 9 August 2022
So glad you were able to stay and experience the tranquility!
About the host
Hosted by Ned Howe
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
Premier Host
They consistently provide great experiences for their guests