Holiday rentals in Lake Shore

Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Rachel's BnB

A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

Waterfront Oasis | Game Room + Fire Pit + Hot Tub

Picture yourself waking up to stunning views of the waterfront and spacious yard, while sipping a fresh warm coffee! Or enjoy a soak in the private hot tub while watching the sunset. For those sports fans we offer a 75" TV and pool table in the well-equipped game room. The outdoor area features a spacious dining setup, perfect for al fresco meals, and a fire pit for evenings of warmth and conversation. Whether you’re lounging by the water or entertaining, this property is the ultimate retreat!

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Relaxing Waterfront Apartment!

Welcome to our Bayhouse StayApartment! Our waterfront getaway features a large dock where you can relax on Adirondack chairs and soak in the beautiful water views! Enjoy kayaking (we have 2 for your use) and feel free to bring your own non motor watercrafts. Roast marshmallows in the our Gazebo's fireplace Inside the apartment you will find a beautiful updated kitchen, comfortable living room, 2 bedrooms and a bonus loft area Full bathroom is upstairs, and downstairs has a half bath.

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.

Captains Quarters Oasis Near Annapolis, Sleeps 4

*Pool is currently undergoing unscheduled maintenance 6/18-7/18* This updated suite is designed for comfort & convenience. Enjoy a king bed and a (queen bed) LoveSac sofa perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!

Luxury 3-Level Townhome Minutes to Annapolis

Visiting the Annapolis area? Stay in style in this very spacious 3-bed, 3.5-bath 3-level townhouse. Sleeps 8 very comfortably in 1 king bed, 2 queen beds, and 2 twin floor mattresses. Two super comfy hang-out areas inside, 2 outdoor living areas, a fully-stocked gigantic kitchen, a large dining room. Comes stocked with all bedding and towels, as well as common guest supplies. Just 14 minutes to downtown Annapolis. Restaurants and shopping are all around. Book your stay today!

Flohom 3 | Tiny Houseboat•Fire Pit•Magothy River

FLOHOM 3 | Bung-a-flo is a Bohemian-inspired floating tiny home for two on the Magothy River. Queen Helix Luxe bed with Parachute linens, a sunlit living space, and a fully stocked kitchen. The rooftop features a fire pit, deep sectional sofa, wool blankets, and 360° river views. Docked at Ferry Point Marina next to an award-winning waterfront restaurant. 15 minutes from downtown Annapolis. A quiet, romantic escape on the water. Welcome aboard. ✨

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

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.