Entire home

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

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Interior
Miscellaneous
Fridge, microwave, oven, stovetop
Point of interest
Beach nearby, sun loungers

Entire home

3 bedrooms2 bathrooms

Popular amenities

  • Washer
  • Parking available
  • Pet friendly
  • Outdoor Space
  • Barbecue grill
  • Air conditioning

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Languages

English

Property amenities

Beach

  • Near the beach
  • Beach sun loungers

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Toaster
  • Ice maker
  • Coffee/tea maker
  • Spices

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bed sheets provided

Bathrooms

  • 2 bathrooms
  • Shower
  • Toilet paper
  • Towels provided
  • Soap
  • Shampoo
  • Hair dryer

Living spaces

  • Fireplace
  • Living room
  • Dining room

Entertainment

  • Smart TV
  • Games

Outdoor areas

  • Patio
  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Firepit

Laundry

  • Washing machine and dryer
  • Near laundromat

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • No elevators
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the waterfront
  • Near a health or beauty spa
  • Near a hospital
  • Near outlet shopping
  • Near a zoo
  • Near the bay

Things to do

  • Fitness facilities nearby
  • Kayak on site
  • Windsurfing nearby
  • Marina nearby
  • Swimming nearby
  • Casino nearby
  • Power boating nearby
  • Horse riding nearby
  • Ice skating nearby
  • Hiking/biking trails nearby
  • Wildlife and game walks nearby

Safety features

  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)

General

  • At least 80% lighting from LEDs
  • Recycling
  • Energy-saving switches

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

This property does not have elevators

Property is also known as

14332

About the neighborhood

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?

Check-out 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 vacation home is within 3 mi (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 mi (5 km).

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