Entire home
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
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Entire home
3 bedrooms2 bathrooms
Popular amenities
- Washer
- Parking available
- Pet-friendly
- Outdoor space
- Barbecue grill
- Air conditioning
Explore the area

Annapolis, MD
- Maryland Quiet Waters Park6 min drive
- Annapolis City Dock9 min drive
- U.S. Naval Academy11 min drive
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)39 min drive
Room options
About the area
Annapolis
Oyster Harbor stay.Your stay at this Oyster Harbor vacation home places you within 3 miles (5 km) of Maryland Quiet Waters Park and Bay Bridge Market Place Shopping Center. Historic Mount Moriah AME Church and Historical Society of Talbot County are also within 3 miles (5 km).
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
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!
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
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 are welcome
- Service animals 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.
Property is also known as
14332
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