See all properties
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

Exterior
Beach
Property grounds
TV, fireplace
Marina

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms122 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

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

Room options

You may also like

Ad
Dining

Best Western Annapolis

Annapolis
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
3.9 out of 5, Good, 1,004 reviews
The price is CA $115
CA $131 total
includes taxes & fees
Jun 7 - Jun 8
Best Western Annapolis

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).
View more Vacation homes in AnnapolisOpens in a new window

What's nearby

  • Maryland Quiet Waters Park - 4 min drive - 3.5 km
  • Bay Bridge Market Place Shopping Center - 4 min drive - 3.5 km
  • Historical Society of Talbot County - 6 min drive - 4.1 km
  • Bay Ridge Beach - 7 min drive - 6.2 km
  • Carrs Beach - 9 min drive - 6.2 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Sammy's Italian Pizza Kitchen - ‬7 min drive
  • ‪Royal Farms - ‬8 min drive
  • ‪Starbucks - ‬5 min drive
  • ‪Oscar’s Coffee - ‬10 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

Dogs allowed with $150 per pet non-refundable fee paid prior to checkin.

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!

Similar properties

Meeting facility
Historic Inns of Annapolis
Historic District
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
4.5 out of 5, Wonderful, 1,858 reviews
The price is CA $144
CA $211 total
includes taxes & fees
Jun 15 - Jun 16
Historic Inns of Annapolis

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

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

  • Pet friendly

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 are welcome
  • Service animals 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
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.
    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

Frequently asked questions

How close is Waterfront Home with Private Dock, Community Beach to the airport?

This vacation home is 23.2 mi (31-min drive) away from the Fort Meade, MD (FME-Tipton) airport, the closest popular airport to the property.

Does Waterfront Home with Private Dock, Community Beach have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Waterfront Home with Private Dock, Community Beach to the beach?

This vacation home is 2.8 mi (7-min drive) from Sparrows Beach and 2.9 mi (8-min drive) from Carrs Beach. Don't forget your sunscreen!

Does Waterfront Home with Private Dock, Community Beach offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Waterfront Home with Private Dock, Community Beach?

No, there is no casino at this vacation home.

What time is check-in at Waterfront Home with Private Dock, Community Beach?

Check-in begins at 4:00 PM.

Is there free parking at Waterfront Home with Private Dock, Community Beach?

Free parking is not available at this vacation home.

Does Waterfront Home with Private Dock, Community Beach have a pool?

This vacation home does not have a pool.

Does Waterfront Home with Private Dock, Community Beach have a spa?

There are no spa services available at this vacation home.

How close is Waterfront Home with Private Dock, Community Beach to downtown Annapolis?

This vacation home is 3.7 mi away from Annapolis.

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

Verified

10/10 Excellent

Michele R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay. Delightful property. Great hosts. Scenic, comfortable and near Annapolis!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Sarah H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, very well stocked house. Quiet and relaxing!
Stayed 5 nights in Aug 2025
Verified

10/10 Excellent

Marketing - E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, cute design and layout, beautiful backyard, safe neighborhood and, tons of parking space in driveway, responsive host
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Calin L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
From a partner site

10/10 Excellent

Andrea V.

Excellent retreat in Annapolis

The home was lovely and very well appointed, having everything we needed for a 3 week stay. We enjoyed daily sunrises from the dock or atrium-style living space; and were surprisingly able to enjoy a few cool enough evenings in August to use the fire pit. The space also allowed us to host a few friends for a brief stay and and a seated dinner for 10. It is super close to downtown Annapolis, just a quick 10-15 minute drive. The hosts were very responsive to any questions or needs we had. We highly recommend this property for anyone looking for a quiet retreat along The Bay.
Verified

10/10 Excellent

Jenn G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
From a partner site

10/10 Excellent

Sarah M.

Amazing choice for young child!

We have a four year old and this was an absolutely perfect place for a get away. We launched kayaks from the dock and the water is calm and easy to navigate. The lawn is great for running and playing. And the beach is so close and set up for little ones. The neighborhood is very family oriented and there were a bunch of kids swimming and plying on the playground. The house has everything you need and the room in back with each is perfect for eating and lounging.

Explore More Ways to Travel with Travelocity