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Waterfront Home with Private Dock, Community Beach

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A two-story house with a front deck, a staircase, and a large sliding glass door.
A wooden pier with two Adirondack chairs facing a calm lake, surrounded by residential buildings under a clear sky.
A marina with wooden docks and a grassy area with houses in the background.
A cozy living room with a fireplace, a television, a sofa, and a bookshelf.
A spacious living room with a large wooden table, comfortable seating, and a view of a deck and outdoor area.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Chesapeake Bay

Popular amenities

  • Patio
  • Barbecue
  • Air-conditioning
  • Internet access
  • Pet-friendly
  • Refrigerator

Explore the area

View map
Annapolis, MD
  • Place, Northern Chesapeake Bay
    ‪1 min walk‬
  • Place, U.S. Naval Academy
    ‪14 min drive‬
  • Place, Annapolis City Dock
    ‪15 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪48 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bunk Room

1 Single Bunk Bed

Front Queen

1 Queen Bed

Loft

1 Double Bed

Waterfront Full

1 Double Bed

2 bathrooms

2nd Full Hall Bath

Toilet · Shower only

Full Hall Bath

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Number of living rooms

Add dates for prices

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About the area

Annapolis

Located on the waterfront, this holiday home is in Oyster Harbor, a neighbourhood in Annapolis. Annapolis Maritime Museum and The Colonial Players are cultural highlights, and some of the area's attractions include Wild Bird Center and French Soldiers Monument. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
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Map
Annapolis, MD

What's nearby

  • Northern Chesapeake Bay - 1 min walk - 0.1 km
  • U.S. Naval Academy - 14 min drive - 7.5 km
  • Annapolis City Dock - 15 min drive - 8.2 km
  • Navy-Marine Corps Memorial Stadium - 17 min drive - 10.0 km
  • Chesapeake Bay Bridge - 30 min drive - 24.1 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪The Beacon Restaurant - ‬8 min drive
  • ‪Royal Farms - ‬8 min drive
  • ‪Grump's Cafe - ‬5 min drive
  • ‪Forward Brewing - ‬9 min drive

Frequently asked questions

Is Waterfront Home with Private Dock, Community Beach pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Waterfront Home with Private Dock, Community Beach?

On-site parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 11:00 AM.

Where is Waterfront Home with Private Dock, Community Beach located?

Located in Oyster Harbor, this holiday home is steps away from Chesapeake Bay and Northern Chesapeake Bay. Maryland Quiet Waters Park and Bay Bridge Market Place Shopping Center are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 15 out of 16 reviews
Rating 8 - Good. 1 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

10/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home.
Stayed 3 nights in Oct 2026
Response from VrboOwner on 26 October 2026
Thanks, Steve! We hope we can host you again soon.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Place is as-advertised. We had a great visit - crabbing is certainly an option.
Stayed 2 nights in Jul 2026
Response from VrboOwner on 1 August 2026
Thanks! Please come stay with us again any time.
Verified review

10/10 Excellent

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
Response from VrboOwner on 4 November 2025
Thanks, Michele! We’re delighted to hear that The Pearl (of Oyster Harbor) provided a wonderful and delightful stay for you. It’s fantastic that you found the property scenic, comfortable, and conveniently located near Annapolis. We’re thrilled to have been your hosts and hope to welcome you back in the future! Sean, iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location was wonderful, nestled in a cute and safe neighborhood. The house was exactly as described, and the management company provided clear instructions and excellent communication throughout our stay. One of the highlights was the beautiful backyard overlooking the water. Enjoying the breathtaking sunrise each morning with a cup of coffee made our stay even more special. We would definitely recommend this property and would love to stay here again!
Stayed 3 nights in Aug 2026
Response from VrboOwner on 19 August 2026
Thanks, Amy! Please come back and stay with us again any time!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, very well stocked house. Quiet and relaxing!
Stayed 5 nights in Aug 2025
Response from VrboOwner on 5 September 2025
Thanks, Sarah! We’re thrilled to hear that The Pearl (of Oyster Harbor) was a great location for your stay. It’s wonderful to know that you found the house well-stocked and enjoyed the quiet and relaxing atmosphere. We would love to host you again next time you’re in town. Melissa~iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely home and property. The house was clean and very pretty. We had a blast with the kayaks and paddle board. It was a very nice quiet neighborhood too. We hope to come back.
Stayed 6 nights in Jul 2026
Response from VrboOwner on 12 July 2026
Thanks, Lynn! We look forward to hosting you again. Sean
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family had the best time at your house! It was nice and clean and had everything we could need. The kids had a blast crabbing and fishing off your dock and we all loved using the kayaks and paddle board. We were able to see the sunrise over the water a few mornings.. so pretty! We hope to come back in the future
Stayed 7 nights in Jul 2026
Response from VrboOwner on 29 July 2026
Thanks! We hope to host you again soon.
Verified review

10/10 Excellent

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
Response from VrboOwner on 14 October 2025
Thanks, Ashlyn! We’re thrilled to hear that The Pearl (of Oyster Harbor) impressed you with its clean and cute design, beautiful backyard, and safe neighborhood. It’s wonderful to know that the ample parking space and our responsiveness met your expectations. We hope to host you again next time you’re in town! Melissa~iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, relaxing and clean property. Loved having the use of the kayaks, grill and firepit. Comfortable beds and bedding. 5 minute walk to the community private small beach. The only negative thing I could say about this property is the loud air conditioning unit in the front room. Thank you to our great hosts!
Stayed 2 nights in Jun 2026
Response from VrboOwner on 16 June 2026
Thanks, Adam! We will look into that AC unit to see if we can quiet it down somehow! We appreciate the feedback and hope to host you again soon. Sean, iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location
Beautiful home, well stocked and the most comfortable beds!There were jellyfish off the dock so we couldn’t swim. We did enjoy the kayaks and paddle board. This was our first time to the area and was not familiar with the lakes and Chesapeake bay.We loved downtown Annapolis. We loved the sun room! And the fire pit.The beach area was invaded by geese and goose poo… :(We enjoyed the games and had an extremely relaxing time.
Stayed 2 nights in Jun 2026
Response from VrboOwner on 13 July 2026
Thanks, Amanda! Sorry for the jellyfish and goose poop, but so glad it was otherwise enjoyable! Please come back and stay with us again. Sean
Verified review

10/10 Excellent

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
Response from VrboOwner on 3 June 2025
Hi Calin! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
From a partner site

10/10 Excellent

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.
Response from VrboOwner on 5 September 2025
Thanks, Andrea! We’re thrilled to hear that The Pearl (of Oyster Harbor) was lovely and well-appointed for your 3-week stay. It’s wonderful to know that you enjoyed the daily sunrises from the dock and atrium-style living space, and that you were able to make use of the fire pit during those cool August evenings. We’re glad the space allowed you to host friends and enjoy a seated dinner for 10. It’s great to hear that the location was convenient for your trips to downtown Annapolis. We appreciate your kind words about our responsiveness and are delighted to know you recommend the property for a quiet retreat along The Bay. We would love to host you again next time you’re in town. Melissa~iTrip Annapolis
Verified review

10/10 Excellent

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
Response from VrboOwner on 20 June 2025
Thanks, Jenn! We’re thrilled to hear you enjoyed your stay at The Pearl (of Oyster Harbor) and that there was room for everyone. It sounds like the kids had a great time with the fire pit! We appreciate your feedback on the kitchen drawers and layout, and we’re glad it didn’t detract from your experience. We’d love to host you and your family again anytime you’re back in Annapolis, hopefully with warmer weather for kayaking! Melissa~iTrip Annapolis
From a partner site

10/10 Excellent

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.
Response from VrboOwner on 20 June 2025
Thanks, Sarah! We’re thrilled to hear you and your family enjoyed your stay at The Pearl (of Oyster Harbor). It sounds like you had a wonderful time kayaking, playing on the lawn, and enjoying the nearby beach. We’re glad the house met your needs and that the family-friendly neighborhood added to your experience. We’d love to host you again anytime you’re back in the area! Melissa~iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect stay on the bay!
Stayed 2 nights in Jun 2026
Response from VrboOwner on 28 June 2026
Thanks Carolyn! We hope to host you again soon. Sean, iTrip Annapolis
Verified review

10/10 Excellent

Stayed 4 nights in Aug 2026
Response from VrboOwner on 12 September 2026
Thanks, Jim. We hope to host you again soon.
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