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New Loft w/South River view from treehouse deck!

Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern apartment that has a treehouse style deck for relaxing and enjoying the outside. The unit is served by a separate entrance and free street parking. Bring your kayak or stand-up-paddleboard, or try your luck at fishing! The TV is upgraded to a 55". Downtown Annapolis is just 6 miles away and offers cultural attractions, bars and restaurants, historical tours and access to the Naval Academy.

Luxury 1BR/1BA Private Suite Close to DC!

Whether you’re looking for a place to stay a couple of days, weeks, or months, this luxurious basement apartment offers a spacious environment with the perfect touch of style, comfort, and sophistication. Enjoy the electric fireplace, office, reading nook, and your own private spa bathroom. This suite has a private entrance and is located in a very peaceful cul de sac with plenty of restaurants and shopping nearby. The home is located just 20 mins outside of DC. Not suitable for small children.

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.

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Spacious 3 Bedrooms House+Patio+Playground

Spacious 3 bedrooms house with functional patio + private playround located in Edgewater, only 15 mins drive to downtown Annapolis. Fully equipped with designer furnitures, with a sense of home! Huge dining room and fully functional kitchen, perfect to enjoy a great evening with your friends and family! Bedrooms are equipped with your own desks if you want to do some works even in your vacation. Easily fit 2 cars in private driveway. Very quiet neighborhood with proximity to everything!

Nautical Charm and relaxing waterview!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchenette (limited-no range), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Annapolis Garden Suite

Welcome! We’re tucked away on a forested residential street, roughly a 7 minute drive from restaurants, coffee shops and all that Annapolis has to offer. 15m from the coast, 30m from Baltimore and 35m from DC. Tl;dr: this is a private ground-level guest suite with 3 beds, 2 bedrooms, 1 desk (optional standing desk), 1 kitchen with oven, dishwasher + Nespresso/pour over, 2 tvs, laundry room with washer/dryer, fast wifi, a pool, patio and a forest view. We live on the top floor.

Renovated Basement with Private Entrance

Fully renovated & updated basement with a full set of windows and sunlight. House is in a very nice and safe neighborhood. Walk-out basement with Private Entrance. Plenty of Parking. Non smoking. All Utilities and Wi-Fi are included. • Total Area: 800 Sq.ft. • One Bedroom with closet • Full Bathroom • Fully Furnished • Kitchen • Dining Area • Walk out Basement – Above ground (Private Entrance) • No Owen • No Dishwasher • No Washer and Dryer • Plenty of Parking • No Smoking

Cozy waterview home in West River!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

Luxury Home, Sleeps 15, Private Pool, Close to DC

Stunning 6 bedroom, 5½ bath home on 34 acres with panoramic woodland views and private salt water pool, perfect for that special gathering. Secluded yet just 35 minutes from Capitol Hill and 20 minutes from Annapolis. The home, with its high ceilings, huge windows and expansive decks comprises over 8000 square feet, so there is plenty of room to stretch out. *** IMPORTANT Please send AN INQUIRY with a little about you PRIOR to requesting a booking.

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.