Located on the waterfront, this holiday home is in Oyster Harbor, a neighbourhood in Annapolis. The area's natural beauty can be seen at Jonas Green State Park and Smithsonian Environmental Research Center, while Annapolis Maritime Museum and The Colonial Players are cultural highlights. Wild Bird Center and French Soldiers Monument are also worth visiting.
Bay Bridge Market Place Shopping Center - 4 min drive - 3.1 km
Historical Society of Talbot County - 5 min drive - 3.8 km
Bay Ridge Beach - 5 min drive - 3.5 km
Carrs Beach - 6 min drive - 4.5 km
Getting around
Odenton Station - 29 min drive
Fort Meade, MD (FME-Tipton) - 31 min drive
Restaurants
McDonald's - 5 min drive
Bay Ridge Wine & Spirits - 5 min drive
Starbucks - 5 min drive
Sammy's Italian Pizza Kitchen - 7 min drive
Royal Farms - 8 min drive
About this property
Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly
Experience the Difference: Professionally Managed by iTrip Annapolis
Welcome to All Decked Out, your dream escape in the waterfront Oyster Harbor Community of Annapolis, a tranquil retreat on the Annapolis Neck Peninsula. This beautifully renovated 4-bedroom, 3-bath home blends modern elegance with timeless coastal charm. With sweeping water views, a private pier, multiple decks, and seamless Chesapeake Bay access, this home is perfect for boating enthusiasts, families, and anyone craving tranquility by the water.
Spacious Coastal Living
The open concept layout is designed for gathering and relaxation.
Expansive windows framing serene waterfront views
Waterfront dining room with seating for 6
Chef’s Kitchen
A true entertainer’s kitchen featuring:
Large island with breakfast bar seating for 4
New stainless steel appliances
Ample prep space
Fully stocked with cookware and dinnerware for 12 guests
Coffee bar in the kitchen (plus a second coffee bar in the Dining Room and a third in the King Suite)
Sleeps 12
Main Level
Double Queen Suite (sleeps 4) with en-suite bath with dual access to Living room
Second Level
Waterfront King Suite with luxury bath, sitting room, coffee bar & deck access
Waterfront Double Queen Bedroom (sleeps 4) with deck access
Full Bedroom
Full Hall bath with shower
Outdoor Living
Private dock
Covered deck + upper waterfront deck
Waterfront patio with built-in grill & outdoor kitchen
Water views from multiple rooms
Bring your boat, kayak, or simply enjoy sunset views from the dock.
Community Perks
Guests enjoy access to Oyster Harbor’s beach, fishing pier, boat ramp, playgrounds, nature trails, and exercise course.
Dog-Friendly - $150 non-refundable fee per pet (paid prior to check-in).
Ideal Location
10 minutes to Downtown Annapolis
12 minutes to USNA
Easy access to DC & Baltimore (33 miles)
Parking for 2-4 SUVs/cars in the circular driveway
Perfect for family gatherings, Navy visits, or peaceful waterfront retreats.
Location Highlights:
Nestled in the quiet Oyster Harbor community, this property is minutes from downtown Annapolis, shopping, dining, and entertainment.
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children
Children allowed: ages 0–17
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Events
No events allowed
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Pets
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
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Frequently asked questions
Is Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly?
As of 4 April 2026, prices found for a 1-night stay for 2 adults at Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly on 9 May 2026 start from NZ$1,340, 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.
How much is parking at Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly?
On-site parking is available at the property.
What time is check-in at Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly?
Check-in begins at 4:00 PM.
What time is check-out at Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly?
Checkout is at 11:00 AM.
Where is Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly located?
Located in Oyster Harbor, this holiday home is steps away from Chesapeake Bay and Northern Chesapeake Bay. Bay Bridge Market Place Shopping Center and Maryland Quiet Waters Park are also within 3 miles (5 km).
Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly Reviews