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Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Newly renovated cottage on 3 acres Annap/DC/Balt

Meadowview Farmhouse is a newly renovated house centrally located between Annapolis, Baltimore and DC. Tour the sights and then return home to the peace and quiet of a 3 acre farm with expansive meadow views. Relax on the large front porch or enjoy dinner and drinks on the back deck looking out over the fields. Everything here is brand new and ready to make this a vacation to remember. Owners have many years of experience hosting and are available to assist with any needs that may arise.

Vanishing Run Retreat with Pool

Escape to this warm and welcoming 4-bedroom, 3-bathroom home in the heart of South County! Perfect for families and groups, this spacious retreat is designed for comfort, relaxation, and making lasting memories. Unwind by the fenced-in pool, let the kids enjoy the large yard and play area, or gather in the expansive eat-in kitchen, perfect for shared meals and quality time. With 7 beds and 3 full bathrooms, there's plenty of space for everyone to spread out, relax, and feel at home.

Modern studio near UMD hospital

Stylish studio basement apartment located 3 minutes from UM Capital Region hospital. As you pull up to our quiet neighborhood you can park right in the drive. The entrance is around the corner to enter your private space. We offer all the essentials needed to have a relaxing stay. The full service kitchen is well equipped and inviting. A large over sized sink for a quick clean up. Come unwind after a long day in this private studio with rainshower and jets. Long stays are welcome.

Home Sweet Home! 3 bds | Bath | Kitch | Laundry

Stay and Relax with the whole family in this brand new spacious basement apartment with lots of room for fun. Easy access to the White House, Six Flags, Chesapeake Beach, National Museums, Smithsonian Zoo, and a host of other beautiful sights in the D.C., Maryland, and Virginia (DMV) areas. The nightly rate includes up to two guests, and there is a $20 per night charge for each additional guest staying overnight in the unit.

South River Park Apartment

Located minutes from Annapolis, the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.

Quiet Farm Stay near Annapolis

Welcome to my little farm. I live here most the time, but love to travel or just go camping so the place is all yours when I'm away. Over 3 acres of great views and pasture only 10 minutes from Annapolis. Close to everything, but surrounded by nature and quiet, chickens and horses. And there's always fresh eggs. Enjoy!

Cozy waterfront getaway on the Bay

This 2 BR renovated waterfront home has a large, modern kitchen, comfy living rm and den, woodburning fp and hot tub. Hi speed FIOS & WiFi. Large pier & deck. Stunning waterfront and sunset views. Enjoy birdwatching, kayaking, or soak in the hot tub!