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Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly

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An aerial view of a residential area with houses, a dock, and boats.
A modern kitchen with a central island, bar stools, and a dining area with a sofa and coffee table.
A bedroom with a tufted headboard, a bed with a beige quilt, a ceiling fan, a sliding door, and a flat-screen TV.
A two-story house with a balcony, a front porch, and a small front yard.
A wooden deck with wicker furniture and a white railing overlooking a lake.
4 bedrooms3 bathroomsSleeps 12

Popular amenities

  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Annapolis, MD
  • Place, Maryland Quiet Waters Park
    ‪4 min drive‬
  • Place, Bay Bridge Market Place Shopping Center
    ‪4 min drive‬
  • Place, Historical Society of Talbot County
    ‪6 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪46 min drive‬

Rooms & beds

4 bedrooms (sleeps 12)

Full Bed Guestroom

1 Double Bed

King Suite

1 King Bed

Main Floor Queen Suite

2 Queen Beds

Waterview Queen Bedroom

2 Queen Beds

3 bathrooms

King EnSuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Main Floor Full Bath

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Upper Level Hall Bath

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Balcony
Number of living rooms

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 (garage parking not included)



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.

Add dates for prices

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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

Property # 4403926vb
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

About the area

Annapolis

Located on the waterfront, this holiday home is in Oyster Harbor, a neighbourhood in Annapolis. Chesapeake Bay Bridge is a notable landmark, and the area's natural beauty can be seen at Chesapeake Bay and Sandy Point State Park. Wild Bird Center and Annapolis Maritime Museum are also worth visiting.
Map
Annapolis, MD

What's nearby

  • Maryland Quiet Waters Park - 4 min drive - 3.5 km
  • Bay Bridge Market Place Shopping Center - 4 min drive - 3.5 km
  • Historical Society of Talbot County - 6 min drive - 4.1 km
  • Bay Ridge Beach - 7 min drive - 6.2 km
  • Carrs Beach - 9 min drive - 6.3 km

Getting around

  • Odenton Station - 29 min drive
  • Fort Meade, MD (FME-Tipton) - 31 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪The Beacon Restaurant - ‬8 min drive
  • ‪Sammy's Italian Pizza Kitchen - ‬7 min drive
  • ‪Royal Farms - ‬8 min drive
  • ‪Starbucks - ‬5 min drive

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 Waterfront home with private pier, dogs?

As of 5 July 2026, prices found for a 1-night stay for 2 adults at Waterfront home with private pier, dogs on 6 July 2026 start from AU$1,537, 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).

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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Languages:

English
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