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Waterfront Home with Private Dock, Community Beach

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Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms122 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • 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 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!
During your stay at this holiday home, you're just a quick walk from Chesapeake Bay. You'll find features such as laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
  • Air-conditioned home with kitchen, washing machine and 2 bathrooms
  • Free WiFi
  • Amenities include laundry facilities
  • Steps from Chesapeake Bay and Northern Chesapeake Bay
Waterfront Home with Private Dock, Community Beach offers its guests barbecue grills and laundry facilities. The front desk is open around the clock.

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 lift
  • Smoke-free property

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

  • No pets allowed, but service animals are welcome

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

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