10/10 Excellent
Michele R.
Oct 26, 2025
Liked: Cleanliness
Michele R.
Stayed 2 nights in Oct 2025
Entire home
Waterfront Home with Private Dock, Community Beach
Vacation home perfectly located for exploring Oyster Harbor
Choose dates to view prices
Photo gallery for Waterfront Home with Private Dock, Community Beach
Reviews
1010 out of 10
Exceptional
Entire home
3 bedrooms2 bathrooms122 sq m
Popular amenities
- Kitchen
- Washer
- Dryer
- Free WiFi
- Air conditioning
- Outdoor Space
Explore the area
Annapolis, MD
- Maryland Quiet Waters ParkPlace, Maryland Quiet Waters Park3 min drive
- Bay Bridge Market Place Shopping CenterPlace, Bay Bridge Market Place Shopping Center4 min drive
- Bay Ridge BeachPlace, Bay Ridge Beach5 min drive
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)38 min drive
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About the area
Annapolis
Oyster Harbor stay.At this Oyster Harbor vacation home, you'll be within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay. Maryland Quiet Waters Park and Bay Bridge Market Place Shopping Center are also within 3 miles (5 km).
What's nearby
- Maryland Quiet Waters Park - 3 min drive - 3.2 km
- Bay Bridge Market Place Shopping Center - 4 min drive - 3.1 km
- Historical Society of Talbot County - 5 min drive - 3.8 km
- Bay Ridge Beach - 5 min drive - 3.5 km
- Carrs Beach - 6 min drive - 4.5 km
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!
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!
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- Pool
- Kitchen
- Washer
- Dryer
Property amenities
Internet
- Available in the house: Free WiFi
Parking and transportation
- Parking on site
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
- 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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.
Property is also known as
14332
Waterfront Home with Private Dock, Community Beach Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 7 out of 7 reviews
10 - Excellent
7
Rating 8 - Good. 0 out of 7 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 7 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 7 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 7 reviews
2 - Terrible
0
9.6/10
Cleanliness
Reviews
10/10 Excellent
Marketing - E.
Oct 7, 2025
Liked: Cleanliness
Clean, cute design and layout, beautiful backyard, safe neighborhood and, tons of parking space in driveway, responsive host
Marketing - E.
Stayed 4 nights in Oct 2025
10/10 Excellent
Sarah H., Southborough, MA
Sep 1, 2025
Liked: Cleanliness
Great location, very well stocked house. Quiet and relaxing!
Sarah H.
Stayed 5 nights in Aug 2025
10/10 Excellent
Jenn G., Cuyahoga Falls, OH
Jun 7, 2025
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.
Jenn G.
Stayed 3 nights in Mar 2025
10/10 Excellent
Calin L.
Apr 22, 2025
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!!
Calin L.
Stayed 3 nights in Apr 2025