Annapolis, Maryland


Properties Available 42 properties available
Overlooking Chesapeake Bay, this charming Annapolis home is nestled in the serene Bay Ridge community, just steps away from a private beach. Bring the whole family together and relish watching gorgeous sunrises and sunsets and taking in panoramic bay views from both levels of this home's wraparound porches. When you aren't lounging and watching yel
The Salty Crab (580902)
Annapolis, MD
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Escape to this charming house in Edgewater, MD, where a beach and play area are just a short walk away. With a water view within 100 yards of the community beach, this spacious and open living design offers a tranquil retreat. Recently furnished with all new furniture and beds, including a king bed on the main floor with an en suite bathroom with a
Adventure Annapolis (606857)
Edgewater, MD
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Located on a quiet and peaceful suburban street, you will have an unforgettable trip to this personal slice of paradise! Perfectly situated in the gorgeous Homewood neighborhood, you'll be just a short walk/bike ride from downtown Annapolis, where a series of amazing attractions await you and your family. Check out the variety of dine-in restaurant
Admiral's Glen (581883)
Annapolis, MD
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
This gorgeous five bedroom home boasts a screened porch, great interiors, and a guests house. Inside, there are many areas to escape to or gather in. A warm formal living room has a fireplace and comfy seating. The French doors open onto a large screenedin porch overlooking the pool. The huge lower level recreation room has a sectional and anothe
The Liberty Club (290828)
Annapolis, MD
House
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Nestled in a family neighborhood between Fishing Creek and the South River, this Annapolis vacation home is great for groups with children, thanks to the various children's sleeping options. It offers a large heated, saltwater pool, and quality furnishings, while is just minutes outside downtown Annapolis. A quick stroll down the street takes you t
Thomas Point Tranquility (290128)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Overlooking Spa Creek, this updated Annapolis condo is perfectly located amidst the city's vibrant entertainment hub. Known for its delicious seafood, sailing, and shopping - there's something for everyone! Attractions like the U.S. Naval Academy Museum, Quiet Waters Park, William Paca House & Garden, Sparrows Beach, and numerous marinas are all wi
USNA Getaway (594693)
Annapolis, MD
House
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 6 guests
Featuring the most sought-after Chesapeake Bay view, this luxurious newly built waterfront Annapolis retreat is ready for you and your family and friends! The porch and balcony are where you will spend most of your time on the rocking chairs or comfy outdoor couch taking in the Chesapeake Bay. The back patio and gardens offer alfresco dining with a
The Ship's Bridge (290394)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Delightfully adorned with nautical charm and soft furnishings, this centrally-located Annapolis home is well-prepared to host you and yours! Nestle down in absolute comfort when you sit on the oversized sofa in the living room and stream your favorite TV shows and movies. When hunger hits, head for the home's full kitchen where you'll be greeted by
The Robins Nest (577178)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Harness Creek waterfront provides a peaceful getaway just five miles to downtown. Custom renovations transformed this waterside cottage into an Annapolis oasis. Enjoy unobstructed views of waterfront views from this beautiful home. The kitchen is all brand new, with a large granite island. It opens to the dining and living area with water views.
Waterfront and Wine (290233)
Annapolis, MD
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Get ready to experience Annapolis from another point of view when you book this upscale traditional residence situated across from St. John's College! The original house was built in the 1960s with original retro tile in bathrooms with modern conveniences. There is wood flooring on the main level. The spacious living room is beautifully, yet comfor
St Johns Adjacent (290395)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 8 guests
Located just a block away from the Chesapeake Bay and Bay Ridge community beaches and a few miles from Annapolis' historic downtown area, this roomy home will be perfect for a memorable family vacation! There are warm and inviting social rooms for gathering, quiet nooks for some me-time, and sprawling outdoor spaces. The large deck overlooking the
Bella Chateau (290092)
Annapolis, MD
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 15 guests
Decorated for a comfortable stay, from the moment you walk inside, you will feel at home. Featuring hardwood flooring, central air-conditioning, and plush furnishings - settle down on the living room's sofa and stream your favorite show. When you aren't dining out at one of the fun Annapolis eateries, the well-equipped kitchen boasts all of the nec
Plebe's Paradise (594961)
Annapolis, MD
House
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests

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