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Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

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Property grounds: BB court, house, barn, pool and grass volley ball court.
Back of house
Large Platform at end of private pier
pool
All purpose sports court with pickleball and basketball

Reviews

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

Popular amenities

  • Free WiFi
  • Air conditioning
  • Parking available
  • Laundry
  • Kitchen
$556
avg per night

Explore the area

View in a map
Taylors Island, MD
  • Place, Blackwater National Wildlife Refuge
    ‪16 min drive‬
  • Place, Harriet Tubman Underground Railroad National Historical Park
    ‪33 min drive‬
  • Place, Gerry Boyle Park at Great Marsh
    ‪40 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪64 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 Twin 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
Price is $556 avg per night

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About the neighborhood

Taylors Island

Located in Taylors Island, this farm stay 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. Be sure to check out the area's animals with activities such as game walks and birdwatching.
View more Agritourism in Taylors IslandOpens in a new window

What's nearby

  • Blackwater National Wildlife Refuge - 16 min drive - 11.7 km
  • Harriet Tubman Underground Railroad National Historical Park - 33 min drive - 34.6 km
  • Harriet Tubman Museum and Educational Center - 37 min drive - 39.9 km
  • Dorchester County Visitors Center - 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

  • ‪Madison Bay - ‬20 min drive
  • ‪Boats & Hose - ‬11 min drive
  • ‪Millie's at Madison Bay - ‬20 min drive
  • ‪McCray's Castaways - ‬20 min drive
  • ‪Marley's Cafe - ‬19 min drive

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.
Our prices include all fees. No hidden fees.

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

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
Parties and events are allowed on site
Note from host: weddings and large functions req. add fee etc.
Safety features at this property include a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock

We should mention

A car is required for transportation to and from this property

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 Mar 28, 2026, prices found for a 1-night stay for 2 adults at Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball on May 15, 2026 start from $556, 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?

Onsite 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?

Check-out is at 10:00 AM.

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

This family-friendly Taylors Island farm stay is located on the waterfront, 5.6 mi (9 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 mi (32 km).

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball Reviews

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 75 out of 85 reviews
Rating 8 - Good. 9 out of 85 reviews
Rating 6 - Okay. 0 out of 85 reviews
Rating 4 - Poor. 1 out of 85 reviews
Rating 2 - Terrible. 0 out of 85 reviews

9.0/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

8/10 Good

Cathleen C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property

Our family had a great time during our stay. We really enjoyed the pool and crabbing off the dock. The house had everything we needed.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Brent W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. Away, but not too far away. We had 3 generations on our vacation and all had a great time!
Stayed 8 nights in Jun 2025
Verified

10/10 Excellent

Corey L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house! Better in person! Thanks Ned! Plan to be back next year
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Petrit N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Lisa S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic for family gathering

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.
Stayed 4 nights in Jun 2025
Verified

8/10 Good

Kim N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 6 nights in Jul 2025
Verified

10/10 Excellent

Wilson G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good place for blue crab

Great place for family and friends
Stayed 4 nights in Aug 2023
Verified

10/10 Excellent

ann r.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Private dock at sunset
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Logan K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Property

Cool house on a breathtaking property, we had a great time and had everything we needed
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Jenny M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Labor Day on the bay

Our group had a lovely visit - we enjoyed the fun amenities and the spacious, private, peaceful property.
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

Hunter A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cambridge trip

Fun place to stay. Very private getaway
Stayed 4 nights in Jan 2023
Verified

10/10 Excellent

Christian S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location with privacy

We very much enjoyed our vacation at your house
Stayed 7 nights in Aug 2022
Verified

10/10 Excellent

Luke H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend getaway

Very beautiful property offering a lot of activities and ways to pass the time.
Stayed 3 nights in May 2022
Verified

10/10 Excellent

Thomas S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family adventure

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.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Samantha M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Private getaway

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.
Stayed 5 nights in Jun 2024
Verified

10/10 Excellent

Aaron N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Renter

This is an amazing property and a terrific place to stay! Highly recommend to any one interested. We stayed for Ironman MD and was perfect!
Stayed 4 nights in Sep 2023
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Serene

If you are looking for a family get away from everyone with tons of space This is the place
Stayed 3 nights in Jun 2022
Verified

10/10 Excellent

Toyin A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Historic Home

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!
Stayed 3 nights in Sep 2022
Verified

10/10 Excellent

James L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good quiet stay in the country

I would book the house. Lots of room and a big kitchen. It is 20-30 minutes from Cambridge and really quiet. It is perfect with a group.
Stayed 3 nights in Sep 2022
Verified

10/10 Excellent

Courtland H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Taylor Isl rental

Property was great house and all was clean and ready . Was a great rental was all as advertised and more. Owner was great.
Stayed 4 nights in May 2019
Verified

10/10 Excellent

Michael C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Taylor Island

The vacation was an opportunity to get away from day to day distractions and spend time with family and enjoy nature.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family getaway

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.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Tina D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

We finally got our family together for a vacation Kids ages 7 months to 9-years old and 6 adults. We couldn’t have picked a better place to stay.There was so much for everyone to do we never had to leave the property. Property sits on 23 acres with an in ground pool which was definitely a plus. Walking to the dock early in the morning to see the sunrise and at night to watch the sunset was so beautiful. I would definitely recommend this house for a family get away. There was 14 of us and we had plenty of room.A big table in the kitchen where we all could sit and eat or outside at the picnic table and watch the kids run around playing. Plus the hammock in the yard was another plus. We had such a great time and made so many memories at this house the kids are already planning our next trip.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Leisa M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tranquil retreat

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
Stayed 7 nights in Jul 2022
Verified

8/10 Good

Douglas W.

Liked: Cleanliness, check-in, communication, location

Family trip

We enjoyed the house and property. It was a laid back vibe vacation. Kids playing and exploring the grounds, first place that we had to bring our own sheets, would have helped to know before booking. Ping pong paddles need replacing but overall we really enjoyed our stay. Loved the big dinning table and view out the back windows. Also crabbing and fishing was a plus! We would stay here again.
Stayed 5 nights in Jul 2024