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Charming Waterfront home, Kent Island, Maryland!
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Reviews
9.0 out of 10
Wonderful
4 bedrooms3 bathroomsSleeps 8255.7 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)34 min drive
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom 1
+2
1 King Bed, 3 Queen Beds and 2 Double Sofa Beds
3 bathrooms
Bathroom 1
Bathtub
Bathroom 2
Bathroom 3
Spaces
Porch or lanai
About this property
Charming Waterfront home, Kent Island, Maryland!
Whether it's relaxation or activity you seek, you'll find it all in the gorgeous waterfront setting of Pier Pleasure, located on Kent Island, Maryland. A hidden gem of Maryland’s Eastern shore. This stunning home is great for swimming, paddle boarding, kayaking from the private dock, playing yard games at the water's edge, and gathering around the fire-pit for s'mores and stories once the sun goes down.
This peaceful, two-story home boasts an expansive piece of property in Harbor View, a private community on a quiet cove just off the Chesapeake Bay. The flat, beautiful lawn stretches all of the way to the dock, where you can enjoy water sports such as paddle-boarding, kayaking or boating (we can help coordinate rentals with local vendors). While you are welcome to dock a boat at the home, please check published depths in the area and familiarize yourself with the waterway.
Pier Pleasure Property Notes: - See Welcome Notes for full Rules/ Regulations after booking.
*** Note: Guest verification will be through the third-party provider “Truvi”. This is done to ensure we are keeping up to date with short-term rental regulations, as well as providing both our guests and our properties with the proper protection. Truvi will contact you via email and/or text to complete the verification process. Please ensure you complete this prior to arriving at the property to enable a quick and easy check-in process. You will be given the choice between a security deposit with a $10 nonrefundable pre-authorization fee or a $35 non-refundable damage waiver; both with protection of up to $500.
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 "All Hands On Deck Property Management House Rules" and shall not engage in any illegal activity.
No Parties allowed. Only registered guests allowed on Property.
Quiet hours are from 10:00 p.m. to 8:00 a.m.
No smoking is permitted anywhere on the premises.
Swim at your own risk
Parking notes: There is free parking available for 4 vehicles on the driveway.
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 back porch facing pier.
This peaceful, two-story home boasts an expansive piece of property in Harbor View, a private community on a quiet cove just off the Chesapeake Bay. The flat, beautiful lawn stretches all of the way to the dock, where you can enjoy water sports such as paddle-boarding, kayaking or boating (we can help coordinate rentals with local vendors). While you are welcome to dock a boat at the home, please check published depths in the area and familiarize yourself with the waterway.
Pier Pleasure Property Notes: - See Welcome Notes for full Rules/ Regulations after booking.
*** Note: Guest verification will be through the third-party provider “Truvi”. This is done to ensure we are keeping up to date with short-term rental regulations, as well as providing both our guests and our properties with the proper protection. Truvi will contact you via email and/or text to complete the verification process. Please ensure you complete this prior to arriving at the property to enable a quick and easy check-in process. You will be given the choice between a security deposit with a $10 nonrefundable pre-authorization fee or a $35 non-refundable damage waiver; both with protection of up to $500.
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 "All Hands On Deck Property Management House Rules" and shall not engage in any illegal activity.
No Parties allowed. Only registered guests allowed on Property.
Quiet hours are from 10:00 p.m. to 8:00 a.m.
No smoking is permitted anywhere on the premises.
Swim at your own risk
Parking notes: There is free parking available for 4 vehicles on the driveway.
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 back porch facing pier.
Add dates for prices
Amenities
Washer
Dryer
Air conditioning
Parking available
Barbecue grill
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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
Safety features at this property include a fire extinguisher
About the area
Chester
Located in Chester, this holiday home is on the waterfront. Queenstown Harbor Golf Links and Queenstown Harbor Golf Club are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Queenstown Premium Outlets and Annapolis City Dock. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium. Take the opportunity to explore the area for outdoor excitement like hiking/biking trails.

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 - 17.3 km
- Chesapeake Bay Bridge - 18 min drive - 17.1 km
- U.S. Naval Academy - 29 min drive - 28.0 km
Getting around
Restaurants
- Chick-fil-A - 5 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
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