Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Top rated by guests
Property grounds: BB court, house, barn, pool and grass volley ball court.
All purpose sports court with pickleball and basketball
1st floor bathroom
2nd floor bathroom
1st floor master bedroom
review stars
9.7Outstanding
(92 Ratings)
"Exactly as advertised. Lots of activities to do for families! Host was very responsive."
Samantha G.
Don't miss out! Price and availability may change
9.7 / 10
Outstanding(92 Ratings)

House in Maryland

14 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

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.

Amenities at Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Non-smoking
No pets allowed

Map of Maryland

city location on map

Ratings and reviews

9.7 / 10
Outstanding(92 Ratings)
10 / 10Outstanding·Jul 2026
Exactly as advertised. Lots of activities to do for families! Host was very responsive.
10 / 10Outstanding·Jul 2026
A wonderful getaway for our family - beautiful, comfortable and perfect place to bring everyone together
10 / 10Outstanding·Jul 2026
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.
10 / 10Outstanding·Jun 2026
This property was absolutely gorgeous and met all our needs for a relaxing family vacation! The house and property was clean and well kept. Although it is an older house, you really can’t tell at all because the owner has put alot of thought and care into restoring it. The kids loved the swimming pool. The pier and waterfront provided great crabbing and fishing. We caught so many crabs in the cove and off the pier. Ned, our host was wonderful to work with. He was quick to respond to all my questions from the beginning to the end. We’re already looking forward to future stays!

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball?

We found 2 amenities for this rental. This includes non-smoking, and no pets allowed.