Waterfront Chesapeake Cottage in Oyster Bay - Dock

Sleeps 83 BR2 BA


Set out to your perfect waterfront vacation rental at ‘The Pearl’, surrounded by vibrant Chesapeake Bay culture and a picturesque waterfront location! Leave this Annapolis home and head downtown to crack open world-famous Maryland Blue Crabs, head to the Navy-Marine Corps Stadium for a football game, or rent a boat or kayak for a day of sailing and paddling on the harbor. After the day’s adventure, return to this 3-bedroom, 2-bath cottage and spend quality time with family around the fire pit!


  • Essentials
  • Central Air Conditioning
  • Free Parking
  • Wireless Internet (WIFI)
  • Deck
  • Beachfront
  • Waterfront
  • Kitchen
  • Washer
  • Pets Allowed
  • Central Heating


Location Details

HISTORIC SPOTS: Maryland State House (4.6 miles), Historic Annapolis (4.7 miles), Historic London Town & Gardens (9.8 miles)

ATTRACTIONS: Quiet Waters Park (3.3 miles), U.S. Naval Academy (4.5 miles) - Museum, Chapel, John Paul Jones Crypt, Navy-Marine Corps Memorial Stadium (5.3 miles)

IN-TOWN: Eastport (3.9 miles), City Dock (4.5 miles), Main Street (4.5 miles), State Circle / Maryland Avenue (4.6 miles), Annapolis Arts District (5.4 miles), Westfield Annapolis (6.6 miles), Annapolis Town Center (6.6 miles)

SEA STOPS: Oyster Harbor Community Beach (0.4 miles), Oyster Harbor Private Community Dock (0.6 miles), Bay Ridge Beach (1.1 miles), Thomas Point Park (2.1 miles), Quiet Waters Park (3.3 miles), Sandy Point State Park (14.0 miles)

EVENTS: Military Bowl - Navy-Marine Corps Memorial Stadium (5.3 miles), Annapolis Film Festival (downtown), Sailboat Show - City Dock (4.5 miles), Power Boat Show, Naval Academy Graduation (4.5 miles)

AIRPORT: Baltimore/Washington International Thurgood Marshall Airport (28.0 miles)


24 reviews
  • Beautiful location close to Annapolis


    We needed a close to Annapolis location for a long weekend and appreciated the down time afforded by this beautiful property. We made use of the kayaks, the well furnished kitchen and spacious sun room. Easy in and out with owners.

    *This review was originally posted on Vrbo

    Ambre C.
    Published December 8, 2021
  • What a Pearl!


    We had a wonderful experience in this lovely home which is directly on the water. Nothing can beat sitting "on the dock of the bay" watching the sunset. This house has everything you need including: well appointed kitchen, amazing views of the water, the best beds EVER, and water toys too! We hated to leave and plan to return as soon as possible.

    *This review was originally posted on Vrbo

    Published October 26, 2021
  • Great place other than the ants.


    Great doc..

    *This review was originally posted on Vrbo

    michael b.
    Published August 25, 2021
    Manager's Response:

    Hi Michael, thanks for letting us know about your stay. After going over your feedback, the homeowner wanted to address the items that you mention:
    - While we didn't find any issue with ants before your check-in, we were glad we could quickly clean and find solutions while you were still in residence.
    - We can assure you that our home receives a thorough cleaning between each guest on the day of arrival.
    - We will contract a pest control service to prevent this issue in the future.
    Thanks again, and we hope that you keep us in mind for your future travels!

  • Excellent Accommodation!!


    Property exceeded expectations. We absolutely loved staying there. Pictures were just like the place. Property manager very helpful. Would definitely go there again.

    *This review was originally posted on Vrbo

    Geraldine G.
    Published August 4, 2021
  • Great stay at The Pearl!


    Had a wonderful time — the house is exactly as described, is nicely renovated and decorated, and very comfortable! The kitchen was stocked with everything we needed and the backyard and dock were great places to relax. Jacki the owner is very friendly and responsive and this is a great place to stay if you're spending time in Annapolis. We will stay here again!

    *This review was originally posted on Vrbo

    John C.
    Published July 19, 2021
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Booking Details

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Property ID: 436807
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