Pier Pleasure Retreat- Waterfront & Private Pier | House in Chester

Pier Pleasure Retreat: Your Waterfront Oasis
Welcome to Pier Pleasure Retreat, a newly renovated 4-bedroom, 4-bathroom waterfront home that blends luxury with relaxation. Perfectly situated along the serene Cox Creek, this stunning retreat offers unparalleled comfort, breathtaking views, and direct access to outdoor adventure. Whether you’re looking to unwind in a tranquil setting or explore the best of the Chesapeake Bay area, Pier Pleasure Retreat is your perfect escape.
Recently renovated with care and attention to detail, this home boasts an open-concept living area filled with natural light and modern coastal décor. The gourmet kitchen is a chef’s dream, featuring a 10-foot island, high-end appliances, and plenty of counter space, ideal for preparing meals to enjoy with family and friends. The spacious living and dining areas offer plenty of room for gathering and making memories.
With 4 bedrooms and 4 bathrooms (2 of which are half-baths), this home comfortably accommodates large groups or families. The stylish bathrooms feature sleek finishes and spa-like touches for an extra layer of relaxation during your stay.
Step outside to the expansive backyard, where you’ll find some of the best sunset views in the area. Whether you’re lounging on the deck, enjoying dinner, or soaking in the scenery, the peaceful atmosphere and stunning vistas will provide the perfect backdrop for your getaway.
Waterfront Bliss:
Your private dock is just steps away, offering direct access to the Cox Creek for kayaking, paddleboarding, or fishing. On-site crab traps are available when crabbing season is open, so you can enjoy the fun of catching your own crabs right from the water—an authentic Chesapeake Bay experience! After a day on the water, retreat to the screened-in porch, where you can relax and unwind while enjoying the sounds of nature around you.
Entertainment for All:
No need to leave the property to find fun! The spacious home is equipped with a 3-in-1 pool, dining, and ping pong table, perfect for hours of entertainment. Whether you want to challenge someone to a game of pool, enjoy a casual meal around the dining area, or engage in a friendly ping pong match, there’s something for everyone. Additionally, enjoy some friendly competition with corn hole boards available for outdoor fun. A variety of board games are also provided to keep everyone entertained during your stay.
As the sun sets, gather around the firepit to make memories and s’mores with loved ones. The cozy warmth of the fire provides the perfect ending to a day spent enjoying the outdoors.
Nearby Attractions:
Though Pier Pleasure Retreat offers a peaceful setting, you’ll find plenty of outdoor attractions nearby. Here are some of the best parks, trails and things to explore:
• Old Love Point Park
• Terrain Nature Park
• Kent Island Cross Island Trail
• Sandy Point State Park
• Blue Heron Golf Course
• Chesapeake Bay Beach Club
• Matapeake Clubhouse and Beach
• Delmarva Balloon Rides
• Chesapeake Bay Environmental Center for kayak or SUP rentals
If you’re attending a wedding on Kent Island, you’ll be just minutes away from two beautiful venues:
• Silver Swan Bayside: A stunning waterfront venue perfect for celebrating your special day, offering beautiful views of the bay.
• Chesapeake Bay Beach Club: A renowned wedding destination offering elegant spaces with spectacular waterfront views.
Explore the beauty of the Chesapeake Bay through hiking, biking, and beachcombing, all just minutes away from your doorstep.
Dining & Entertainment:
When hunger strikes, you’ll find some of the best local dining options nearby. Whether you’re in the mood for fresh seafood or a laid-back beach bar, these spots offer a great mix of flavors:
• Harris Crab House
• Bridges Restaurant
• Fisherman’s Inn
• The Jetty
• Red Eye’s Dock Bar
• Dock House
• Kentmorr Beach Bar & Grill
• The Narrows Restaurant
Enjoy a delicious Maryland crab feast, savor fresh seafood, or sip on a refreshing cocktail while taking in the stunning views of the Chesapeake Bay.
Why You’ll Love It Here:
• Recently renovated with stylish, modern finishes throughout
• Gourmet kitchen with a 10-foot island, perfect for preparing meals together
• Private dock with access for kayaking, fishing, paddleboarding, and crabbing (seasonal)
• Best sunset views in the area, right from your backyard
• Screened-in porch to relax and enjoy the outdoors in comfort
• Proximity to local parks, trails, beaches, and dining hotspots
• Only 3 miles from the iconic Bay Bridge
• Entertainment options with a 3-in-1 pool, dining, and ping pong table, corn hole boards, plus board games for fun indoor and outdoor activities
• Gather around the firepit to make memories and s’mores under the stars
Whether you’re looking to relax by the water, explore nearby attractions, or indulge in the local dining scene, Pier Pleasure Retreat offers everything you need for a memorable getaway. Book your stay today and experience the ultimate waterfront escape!
Pier Pleasure Property Notes:
• You must be 25 years or older to rent this property.
• No pets allowed in/on the home
• Check-in time: 4:00 p.m.
• Check-out time: 10:00 a.m.
• All guests shall abide by local laws and ordinances as well as the House Rules and shall not engage in any illegal activity.
• Quiet hours are from 10:00 p.m. to 8:00 a.m.
• No smoking is permitted anywhere on the premises.
• Parking notes: There is free parking available for 4 vehicles.
• Guest entry instructions: This rental utilizes an E-lock, a digital lock that requires a unique code to enter. This code is reset after each guest’s stay. Guests will receive the door code 2 hours prior to check-in.
• Security camera details: Front door and towards dock

Pier Pleasure Retreat- Waterfront & Private Pier is located in Chester. Pier Pleasure Retreat- Waterfront & Private Pier provides accommodation, featuring Child Friendly, Laundry, TV, among other amenities. This House features Child Friendly, Laundry, TV, to make your stay a comfortable one.

Pier Pleasure Retreat- Waterfront & Private Pier has 4 Bedrooms , 3 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Chester has interesting places to visit. If you want to learn more about the House in Chester, such as places to visit and things to do nearby, you can check below to learn more.