Entire home
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
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3 bedrooms2 bathroomsSleeps 8
Popular amenities
Explore the area

Annapolis, MD
- Maryland Quiet Waters Park6 min drive
- Annapolis City Dock9 min drive
- U.S. Naval Academy11 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!
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
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
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.

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
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
Reviews
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About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan

Languages:
English
Premier Host
They consistently provide great experiences for their guests
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