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Kent Island Beach House - "Pink" House in Kentmorr

KI Beach House – 1,800 sq ft. Chesapeake Bay water views. Across from Channel Side (previously Kentmorr Beach Bar & Restaurant), Kentmorr Marina & charters, and minutes to local wedding venues & Matapeake Beach. Perfect for holidays, wedding accommodations, small family gatherings, fishing trips, or golf getaways. Features 4 bedrooms/3 baths (4th is a large family room with smart TVs & fireplace), kitchen, open dining/living, spacious deck, huge yard, and your own private beach volleyball court.

Waterfront South River Edgewater Sunrises & Beach!

Gorgeous sunrises from your living room & bedroom! Enjoy true nature and explore Selby Bay on the South River! Super clean and charming with water views from kitchen, dining, living room & front terrace! Situated in a quiet neighborhood within 15 minutes from Annapolis & the Naval Academy & 50 minutes from Washington, DC. Your private bedroom & bathroom are located on the first floor of the home. Located directly across the street from our community beach with swimming net and slide, pier & more

Peaceful Waterfront Oasis

This peaceful Chesapeake Bay retreat offers an escape from daily life, with stunning bay views providing a calming backdrop at sunrise and sunset. Relax on the deck with coffee, swim right off the dock, or unwind by the water’s edge. For adventure, take out the available kayaks or paddle board to explore the tranquil bay. Afterward, enjoy a rinse in the outdoor shower and soak in the hot tub under the stars. This serene haven blends relaxation and adventure in a beautiful, picturesque setting.

Cozy Cottage

Escape to this beautiful cottage overlooking the Chesapeake Bay. Just steps from the beach, this getaway offers water views right from the comfort of the living room. The interior has been remodeled and stylishly furnished, with two bedrooms and one bathroom. This cottage is perfect for couples, small families, or a peaceful solo retreat. Minutes from Downtown Annapolis, the Naval Academy, and other points of interest. NOTE: currently doing yard work; the backyard does not have grass yet

Wonderful Cottage Nestled On Chesapeake Bay

Stunning home a short walk from Chesapeake Bay - a perfect blend of comfort and coastal charm. Stroll, jog or bike in the scenic neighborhood. Hear birds, see deer or watch sailboats glide by. Open-concept design and natural light make our home ideal for entertaining, working from home, or relaxing on the spacious deck. Minutes from local eateries and attractions in downtown Annapolis. One dog max 25 lbs allowed; must be fully potty-trained, included on reservation with applicable pet fees.

Beachside Dream

Kick back and relax in this calm, stylish space, 4 bedroom 3 full bathroom, Sandy Beach front, stunning sunset. An hour from DMV. Wall of windows in the Living Room overlooks the evening sunsets on the Bay. Sun room with the stunning views of bay. Spacious rooms for up to 12 guests($50 charge per guest after 8 guest) 10 minute drive from popular wedding venues, Chesapeake Bay Beach Club and Silver Swan. Hotel quality linens and towels are provided, unlimited High Speed WIFI , 3- Smart TV

Franklin At The Bay. Bay Adventures!

Come stay with us at Franklin At The Bay in Deale, Md. This 4BR/3BA retreat is 2 blocks from the Chesapeake Bay! Beautifully appointed for style and comfort. Vacation in fun Franklin Manor, featuring private waterfront park, secluded beach, fishing/crabbing piers, small boat/kayak ramp, boat ramp, swimming, playground, basketball, volleyball, baseball. Fast Wi‑Fi and smart TV. 20 min to Herrington Harbor, 30 min to Annapolis, 1 hour to Baltimore/DC. Book USNA Graduation/Commissioning Week!

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Flohom 14 | Chesapeake Bay • Pool & Beach Access

FLOHOM 14 | Soteria is a coastal-designed luxury houseboat for two on the Chesapeake Bay at Patapsco Marina in Pasadena, MD. Queen Helix Luxe bed with Parachute linens, sunlit living area, fully equipped kitchen, and Starlink WiFi with a dedicated workspace. Rooftop fire pit, dining table, sectional, and panoramic bay views. Marina includes seasonal pool, beach access, grills, and fishing charter access. Baltimore and Annapolis are a short drive. The quiet you didn't know you needed. ✨

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

Spa Creek Condo | Pool, Deck & Parking

Wake up to water views in this updated 1-bedroom Eastport condo overlooking Spa Creek. Step onto the covered deck to watch sailboats drift by, cool off in the community pool, or walk to Downtown Annapolis and USNA in minutes. The pullout sofa adds sleeping space for extra guests, and the full kitchen has everything you need. Two free parking spots right outside the building. A quiet waterfront home base for couples or small groups exploring Annapolis.

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190