The Pearl (of Oyster Harbor)
Annapolis, Maryland
Amenities
A/C
Parking
Washer & Dryer
Scenic Views
Patio/Balcony
Pets Allowed
Home details
Bedroom 1
1 queen bed
Bedroom 2
1 bunk bed
Bedroom 3
1 full bed
Living room
1 full bed
Experience the Difference: Professionally Managed by Property Manager Annapolis
Waterfront 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
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!
License: 000346
All stays include
At Homes & Villas by Marriott Bonvoy we believe certain amenities should be standard.
24/7 support
Kitchen essentials
Starter kit of bathroom amenities
High-speed wifi
Professional cleaning
Premium linens and towels
Television
Digital free stays
Our Tiny Home rentals may not include all essential amenities inside the home.
About the area
Annapolis, Maryland, is a delightful destination that provides a myriad of experiences for its visitors. As Maryland's capital and one of the oldest cities in America, Annapolis is deeply rooted in history and tradition. The city's historic district houses beautifully maintained 18th-century structures, including the Maryland State House, which functioned as the nation's capital post the Revolutionary War.
Often dubbed as "America's Sailing Capital," Annapolis' maritime legacy is palpable in its lively harbor and numerous sailing events. Tourists can partake in boat tours, learn sailing or simply observe yachts and sailboats from waterfront eateries.
The United States Naval Academy is another significant attraction in Annapolis. Guided tours provide a glimpse into midshipman life and naval history. The campus itself is picturesque with Beaux-Arts architecture and views of the Severn River.
For art and culture enthusiasts, Annapolis offers a dynamic arts district featuring galleries that display local artists' work. The city also organizes various cultural festivals throughout the year celebrating music, film, art, among other things.
Nature aficionados will find Quiet Waters Park appealing with its hiking or biking trails, picnic spots, and breathtaking views over South River. For those who prefer beaches, Sandy Point State Park presents sandy shores with vistas of Chesapeake Bay Bridge.
Culinary explorers will appreciate Annapolis' food scene which highlights fresh seafood from Chesapeake Bay including renowned Maryland crabs. There are also ample opportunities to taste local craft beers at one of many breweries in town.
In summary, Annapolis merges history, maritime traditions, natural beauty and a vibrant arts scene to offer a distinctive travel experience that caters to all kinds of travelers.
House rules
Check-in 4:00 PM • Check-out 11:00 AM
Payment & Cancellation
Required Identification Number:000346