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Villa Annapolitana • Parking 1 min • USNA 4 min

Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek lounge area, it’s a perfect place to relax and unwind. The fully stacked kitchen is ready and waiting for you to cook a perfect meal and enjoy a glass of wine. The location is ideal, with the US Naval Academy just a 5-minute walk away. If you are looking for a peaceful escape or a fun vacation, our property has something for everyone. ✔ King Beds ✔ Smart TVs ✔ Sport Equipment

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

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. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

Hot Tub Haven: Annapolis Backyard Oasis

A serene escape awaits you at our cozy 4-bedroom retreat, just minutes away from Historic Downtown Annapolis. As the sun sets, the deck comes alive under the soft glow of string lights beckoning you to unwind in our 8-person Bullfrog hot tub or outdoor firepit where your worries will melt away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Historic Annapolis has to offer!

The Naval Nook 1.3 mi. from Downtown Annapolis

Welcome to your home away from home at the Naval Nook! ~ 4 min. Uber from Downtown Annapolis ~ Brand New Hot Tub ~ Cool Electric AC ~ King Bed ~ Sunroom with Daybed and Trundle ~ Zero Gravity Chairs ~ Outdoor Dining table ~ Beautiful Spacious & Comfortable bedrooms ~ Couch w/ Queen Bed pullout ~ 4 Smart TVs in each bedroom & living room ~ Tiled showers w/ shampoo & conditioner ~ Fully equipped kitchen ~ Luxurious Linens ~ Luxury Electric Fireplace Airbnb Registration #: STR23-145225

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

Cozy Annapolis Cottage.

Stay in the heart of Annapolis! 1 Gig Internet speeds. 220v outlet for EV charging (bring your own cable).Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly renovated. Professional cleaning team with every turnover of the house. Stay in the comforts of your own home and experience all that Annapolis has to offer. Art throughout home by local artist Amy Holt Cline.

12 M to Naval Acadmey | Waterfront

Discover the perfect blend of tranquility and convenience at our charming waterfront property. Nestled away in a serene setting yet close to all the action, this home offers an ideal escape. Imagine unwinding on the expansive screened-in porch, taking in the peaceful views of calm waters, or dropping a crab pot to catch some of Maryland's renowned Blue Crabs.