Entire home
Pier Pleasure Retreat- Waterfront & Private Pier
Photo gallery for Pier Pleasure Retreat- Waterfront & Private Pier





4 bedrooms2+ bathroomsSleeps 10250.8 sq m
Popular amenities
Explore the area
Chester, MD
- Paul Reed Smith Guitars9 min drive
- Matapeake State Park10 min drive
- Chesapeake Bay Bridge18 min drive
- Annapolis, MD (ANP-Lee)32 min drive
Rooms & beds
4 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 Queen Bed
Bedroom 4
1 Queen Bed
Living Room 1
2 Single Futons
2 bathrooms, 2 half bathrooms
Bathroom 1
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Jetted bathtub · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 3
Soap · Towels provided · Toilet
Bathroom 4
Soap · Towels provided · Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Outdoor play area
Garden
Dining area
About this property
Pier Pleasure Retreat- Waterfront & Private Pier
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
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
Property manager
Mei
Languages
English, Spanish
Add dates for prices
Amenities
Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space
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House Rules
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
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
On-site parties or group events are strictly prohibited
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
We should mention
This property does not have any lifts
About the area
Chester
Chester is home to this holiday home. Chesapeake Bay Bridge and Maryland World War II Memorial are local landmarks, and some of the area's attractions include Paul Reed Smith Guitars and Helen Avalynne Tawes Garden. Travelling with kids? Consider French Soldiers Monument, or check out an event or a game at Alumni Hall.
Chester, MD
What's nearby
- Paul Reed Smith Guitars - 9 min drive - 6.6 km
- Matapeake State Park - 10 min drive - 9.4 km
- Sandy Point State Park - 18 min drive - 17.4 km
- Chesapeake Bay Bridge - 18 min drive - 17.4 km
- U.S. Naval Academy - 29 min drive - 29.6 km
Getting around
Restaurants
- Chick-fil-A - 4 min drive
- McDonald's - 5 min drive
- Starbucks - 8 min drive
- Cracker Barrel - 8 min drive
- Pour House Pub - 6 min drive
Frequently asked questions
Reviews
Reviews
No reviews yet
Be the first to leave a review for this property after your stay.
About the host
Hosted by Mei

Hi, I’m Mei, and I’m so excited to host you at Pier Pleasure Retreat! My husband, Rob and I, along with our lovable Goldendoodle, Mars, cherish spending time at our waterfront home. We love to travel, explore new places, and unwind by the water, and we hope you’ll experience the same sense of relaxation and joy here.
We look forward to sharing our home with you and ensuring your stay is as peaceful and enjoyable as possible!
We look forward to sharing our home with you and ensuring your stay is as peaceful and enjoyable as possible!
Languages:
English, Spanish
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