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Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

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Welcome to The Pearl (of Oyster Harbor)!
One of the home's 4 sleeping spaces, this bedroom has a serene view of the water.
View of the lush private waterfront backyard from the home's pier on Oyster Bay.
There's plenty of seating in the family room for the whole crew.
Enjoy quiet mornings on the private pier.
3 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Dryer
  • Fireplace
  • Parking available
  • Washer
  • Pet-friendly
  • Outdoor space

Explore the area

Map
Annapolis, MD
  • Maryland Quiet Waters Park
    ‪6 min drive‬
  • Annapolis City Dock
    ‪9 min drive‬
  • U.S. Naval Academy
    ‪11 min drive‬
  • Annapolis, MD (ANP-Lee)
    ‪17 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bunk Room

1 Single Bunk Bed

Front Queen

1 Queen Bed

Loft

1 Double Bed

Waterfront Full

1 Double Bed

2 bathrooms

2nd Full Hall Bath

Toilet · Shower only

Full Hall Bath

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Separate dining area
Garden
Dining area

About this property

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Available for Commissioning Week 2025!

Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Welcome to the Pearl of Oyster Harbor – a tranquil waterfront retreat on the Annapolis Neck Peninsula. This charming cottage offers the best of all worlds: stunning natural beauty, water activities, and modern comforts.

Outdoor Features:
Private dock for boating, kayaking (3 total kayaks: two adult and one youth), or paddleboarding (inflatable SUP included)
Expansive lawn perfect for cornhole, yard games, or simply soaking up the view
Firepit for cozy evenings with s'mores and stories
Hammock for relaxing with a good book or simply enjoying nature
Parking for 3-4 cars on the driveway

Indoor Highlights:
Bright, airy sunroom with harbor views for board games and family time
Sleek, modern kitchen with large picture windows framing the waterfront
Living room featuring a smart TV and gas fireplace for cozy evenings
Small desk and WiFi printer for remote work convenience

Neighborhood amenities:
Swimming beach
Exercise: Beach volley ball court, 1-mile exercise circuit course, 12' climbing wall, 16' rope climb,
Fishing pier and boat ramp
Playgrounds, nature preserve, picnic areas, beach gazebos

Starter Amenity Pack:
We've got you covered with essentials to make your stay stress-free, including:
Coffee, sweeteners, dish soap, and paper towels
Soap, shampoo, conditioner, and hand sanitizer
Freshly-laundered sheets and towels for every guest

Sleeping Arrangements (3 BR / 2 BA, Sleeps 8):
Front Queen Bedroom: Queen bed, shared full bath in the hall
Waterfront Bedroom: Full bed, shared full bath in the hall
Bunk Bedroom: Twin bunk beds (two twins), shared hall bath
Loft: Full bed above the living room

House Rules:
Family rentals only; one guest must be at least 25 years of age
Dog-friendly (please clean up after your pet) with $150 fee paid prior to check-in
No smoking, parties, or events
Quiet hours from 9:00 pm to 8:00 am
Check-in: 4:00 pm | Check-out: 11:00 am

Property Distance to:
-Downtown Annapolis – 4 miles (10 mins)
-U.S. Naval Academy – 4.5 miles (12 mins)
-Washington, DC – 35 miles
-Baltimore - 20 miles

Create lasting memories at The Pearl (of Oyster Harbor), where waterfront tranquility meets thoughtful amenities and outdoor fun. Book your stay today for an unforgettable Chesapeake Bay escape!

Property manager

iTrip Vacations Annapolis - Sean Degnan
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

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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

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

Annapolis

Located on the waterfront, this holiday home is in Oyster Harbor, a neighbourhood in Annapolis. Annapolis Maritime Museum and The Colonial Players are cultural highlights, and some of the area's attractions include Wild Bird Center and French Soldiers Monument. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Annapolis, MD

What's nearby

  • Maryland Quiet Waters Park - 6 min drive - 4.5 km
  • Annapolis City Dock - 9 min drive - 7.1 km
  • Annapolis Maritime Museum - 10 min drive - 6.9 km
  • Navy-Marine Corps Memorial Stadium - 11 min drive - 8.8 km
  • U.S. Naval Academy - 11 min drive - 8.1 km

Getting around

  • Odenton Station - 26 min drive
  • Fort Meade, MD (FME-Tipton) - 31 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Little Italy - ‬7 min drive
  • ‪Boatyard Bar & Grill - ‬9 min drive
  • ‪Carrol's Creek Cafe - ‬9 min drive
  • ‪Annapolis Yacht Club - ‬9 min drive

Frequently asked questions

Is Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks?

Check-in begins at 4:00 PM.

What time is check-out at Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks?

Checkout is at 11:00 AM.

Where is Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks located?

Located in Oyster Harbor, this holiday home is within 3 miles (5 km) of Maryland Quiet Waters Park, Bay Bridge Market Place Shopping Center and Historic Mount Moriah AME Church. Historical Society of Talbot County and Annapolis Golf Club are also within 3 miles (5 km).

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About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests