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Waterfront Home with Private Dock, Community Beach

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Marina
3 bedrooms, iron/ironing board, free WiFi
Exterior
Beach

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms1316 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Annapolis, MD
  • Place, Maryland Quiet Waters Park
    ‪3 min drive‬
  • Place, Bay Bridge Market Place Shopping Center
    ‪4 min drive‬
  • Place, Bay Ridge Beach
    ‪5 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪38 min drive‬

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About the neighborhood

Annapolis

With a stay at this vacation home in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay. .This vacation home is 0.1 mi (0.1 km) from Northern Chesapeake Bay and 2.3 mi (3.6 km) from Bay Bridge Market Place Shopping Center.
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What's nearby

  • Maryland Quiet Waters Park - 3 min drive - 2.0 miles
  • Bay Bridge Market Place Shopping Center - 4 min drive - 2.0 miles
  • Historical Society of Talbot County - 5 min drive - 2.4 miles
  • Bay Ridge Beach - 5 min drive - 2.2 miles
  • Carrs Beach - 6 min drive - 2.8 miles

Getting around

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

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Bay Ridge Wine & Spirits - ‬5 min drive
  • ‪Starbucks - ‬5 min drive
  • ‪Sammy's Italian Pizza Kitchen - ‬7 min drive
  • ‪Royal Farms - ‬8 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.

Waterfront Home with Private Dock, Community Beach

Experience the Difference: Professionally Managed by iTrip 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!
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace. There's a private patio. A kitchen is outfitted with a refrigerator, a microwave, and a dishwasher. Complimentary wireless internet access is available to keep you connected.
Make use of convenient amenities, which include barbecue grills and bike storage.
Guests will find features like internet access.

Property amenities

Internet

  • Available in the house: Free WiFi

Kitchen

  • Coffee/tea maker
  • Dishwasher
  • Ice maker
  • Microwave
  • Refrigerator

Dining

  • Dining table

Bedrooms

  • 3 bedrooms

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shampoo
  • Shower

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Service animals only (pets not allowed)

Suitability/Accessibility

  • No elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the waterfront

Things to do

  • Bicycle parking
  • Bicycle storage

Safety features

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

General

  • At least 80% lighting from LEDs
  • Bicycle parking
  • Bicycle storage
  • Energy-saving switches in guestrooms
  • Recycling
  • Unit size: 1,316 square feet

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
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed (service animals are welcome, and are exempt from fees)

Children and extra beds

Children are welcome

Events

No events 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
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

Waterfront Home with Private Dock, Community Beach Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

9.6/10

Cleanliness

Reviews

10/10 Excellent

Michele R.

Liked: Cleanliness
Wonderful stay. Delightful property. Great hosts. Scenic, comfortable and near Annapolis!
Stayed 2 nights in Oct 2025

10/10 Excellent

Marketing - E.

Liked: Cleanliness
Clean, cute design and layout, beautiful backyard, safe neighborhood and, tons of parking space in driveway, responsive host
Stayed 4 nights in Oct 2025

10/10 Excellent

Sarah H., Southborough, MA

Liked: Cleanliness
Great location, very well stocked house. Quiet and relaxing!
Stayed 5 nights in Aug 2025

10/10 Excellent

Jenn G., Cuyahoga Falls, OH

Liked: Cleanliness

Nice location in quiet neighborhood

We enjoyed our stay. The house is laid out a bit quirky, but there was room for everyone and it had everything we needed. The kids really enjoyed the fire pit and I wish it would’ve been warmer so we could have used the kayaks.We were able to access downtown Annapolis very easily for a walking tour and a visit to the Naval Academy. The drawers in the kitchen are a bit odd, however we found everything eventually.Overall, great stay and no complaints.
Stayed 3 nights in Mar 2025

10/10 Excellent

Calin L.

Liked: Cleanliness

Great location on the water with a dock!

We had a great Springtime vacation with kids and a grandparent - our kids enjoyed kayaking and paddle boarding from the doc and gramps was very comfortable watching from the yard. It’s a very convenient location for a family. House was small but had everything we needed and well maintained. We recommend it!!
Stayed 3 nights in Apr 2025