The Pearl (of Oyster Harbor)

3 BR
2 Baths
Sleeps 8

About

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!

1246 Washington Dr Annapolis, MD 21403
Registration Number: 000346

Sleeping Arrangements

Front Queen Queen
Bunk Room Bunk Twin
Waterfront Full Full
Loft Full

Bathroom Configuration

Full Hall Bath: Shower, Toilet
2nd Full Hall Bath: Shower, Toilet

Property Rules

Check In: After 4pm
Check Out: Before 11am
Smoking: Not Allowed

Amenities

Air Conditioning
BBQ Grill
Bath Towels
Bay View
Beach chairs
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Clothes Dryer
Coffee Maker
Community Beach
Cooking basics
Dedicated work space
Den
Dining room
Dishwasher
Disinfected
Enhanced Cleaning
Essentials
Family-friendly
Firepit
Fireplace
Full Kitchen
Hair Dryer
Hammock
Heating
Ice Maker
Internet
Internet Access
Iron and Board
Kayaks
Kitchen
Laundry
Living room
Microwave
Open Patio
Parking Available
Patio
Pets Considered
Private Backyard
Private Pier
Private entrance
Refrigerator
Self Check-In
Shampoo
Smoke Detector
Smoke alarms
Sojo Amenity Kit
TV
WIFI
Washing Machine
Water View
Waterfront
body wash
conditioner
hot water
Wifi

Map

Frequently Asked Questions

AGREEMENT

Tenant is at least 25 years old and will be an occupant of the unit The Pearl (of Oyster Harbor). Should any unauthorized persons occupy or use the Premises, Tenant shall vacate the premises immediately without any refund.

BALANCE

Balance is due 30 days prior to arrival date and includes a refundable damage deposit. The balance is due on _BalanceDueDate_. Payment may be made by major credit card. 

CANCELLATION POLICY

Cancellations must occur at least 30 days prior to arrival date, or WILL BE CHARGED THE FULL AMOUNT. If cancellation occurs 30 days or more prior to arrival date all monies will be refunded with the exception of a $100.00 administrative fee.

HAZARDOUS PRACTICES

No BBQ grills of any kind are permitted in the unit. No open flames permitted in the unit.

DOGS OK WITH NON-REFUNDABLE DEPOSIT/Must Be Leashed in the yard

If you wish to bring your dog, you will need to pay the $150 non-refundable pet deposit per pet prior to arrival.  If you bring an unathorized pet on to the property, you will be asked to vacate immediately with no refund of rent or damage deposit. Homeowner and Agent assume no responsibility for any illness or injury that may occur to pets or humans while on the premises. Homeowner and Agent assume no responsibility for the behavior of the pet(s); that responsibility is the Tenant owner. The yard is not completely fenced in here, so please keep your dog on a leash to make sure it does not leave the backyard & bother the neighbors or leave the property.

FALSIFIED RESERVATION

Any reservation obtained under false pretense will be subject to forfeiture of reservation deposit, damage deposit, and/or balance of rental payment.

HOUSEKEEPING

There is no daily maid service. Linens and towels are included and not to be taken from the unit. There is a $_CleaningFee_ one time cleaning fee.

UTILITIES

No compensation will be given for temporary outage of electricity, gas, water or cable. 

NONSMOKING UNIT

Your damage deposit will be forfeited and you will incur an additional charge for cleaning and deodorizing if any evidence of smoking is found.

ENTRY BY OWNER

Owner or owner's agents may enter the premises: in case of an emergency; to make any necessary or agreed upon repairs, alterations, or improvements; supply necessary or agreed upon services or show the premises to prospective purchasers, renters or contractors.  24 hours notice of Owners intent to enter will be given (except in the case of an emergency).

RULES AND REGULATIONS

  1. Tenant agrees to leave the premises and its contents in the same condition, neat and tidy, as Tenant found the premises to be upon move-in, normal wear and tear expected. Please leave all used towels on the floors of the bathrooms and beds linens should all be left on each bed for housekeeping.
  2. All dishes are to be washed and all garbage removed from the premises and placed in outside receptacles. If these items are not completed, the guest will be charged an additional cleaning fee. 
  3. The maximum number of occupants shall not exceed 8 people, not including a child in a crib.
  4. Furnishings are not to be removed from the premises for use outside or in other properties.
  5. No Smoking.
  6. Reservations are not made by or for a minor, defined as any person under the age of 25.
  7. Tenant and any guest of Tenant shall obey all laws of the state of Maryland, as well as local laws, at all times while they are on the premises. Failure to abide by the laws of Maryland or the above rules may cause tenant to be asked to vacate the premises and forfeit all rents and security/damage deposits.
  8. All noise must be brought inside by 10pm. Failure to do so could result in a $500 fine.

SLEEPING CAPACITY/DISTURBANCES

Tenant and all other occupants will be required to vacate the premises and forfeit the rental fee and security deposit for: Occupancy exceeding the sleeping capacity of 8 people, using the premises for illegal activity, causing damage to the premises rented or to any of the neighboring properties and any other acts which interferes with neighbors' right to quiet enjoyment of their premises.
 

HOLD HARMLESS

iTrip or the Owner, does not assume any liability for loss, damage or injury to persons or their personal property. Neither does owner accept any liability for any inconveniences, damage, loss or injury arising from any temporary defects or stoppage in supply of water, gas, cable service, electricity or plumbing, as well as due to weather conditions, natural disasters, acts of God, or other reasons beyond its control.
 

MAINTENANCE

Please report any maintenance needs for the premises to the us and we will respond as quickly as possible. Refunds will not be made for maintenance issues including, but not limited to heating and air conditioning, appliances, televisions, and stereos.

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Phone (410) 571-4076