Annapolis showing street scenes and a city as well as a small group of people

Anne Arundel County Vacation Rentals

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Top Cities in Anne Arundel County

Featured Vacation Homes in Anne Arundel County

Enjoy meals in the spacious kitchen and dining area with a central island and large window offering a view of the outdoors.

"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "

"It was great!"

Enjoy serene waterfront views and easy access to moorings and facilities.

"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"

Enjoy the view from this home's deck, overlooking the city street below.

"Great location in quiet neighborhood."

Enjoy cooking in this well-lit kitchen with a central island, wooden cabinetry, and stainless steel appliances.

"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "

Enjoy cooking in this well-equipped kitchen with a refrigerator, dark wood cabinetry, and a window with blinds.

"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "

CA $102 total

includes taxes & fees

Sep 6 - Sep 7

Stunning two-story home with a charming entrance, complete with a wreath-adorned door and a cozy porch.

"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."

Enjoy a serene view of the water from this deck, surrounded by lush greenery and a comfortable seating area.

"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"

Enjoy cooking and dining in this well-equipped kitchen with appliances and a central island.

"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."

"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."

CA $779 total

includes taxes & fees

Aug 18 - Aug 19

Enjoy a room with a sliding glass door leading to a balcony offering a water view.

"We wanted to celebrate Easter with our two daughters who go to Loyola in Baltimore so we decided to stay in Annapolis area. We absolutely loved the house. The location and view was amazing- right on the Chesapeake bay! The house was clean and welcoming. There were so many nice little touches that made us feel welcomed. We had a great weekend celebrating Easter with our two daughters and son. The house was the perfect size for the 5 of us. "

Stroll through the charming outdoor corridor to a cozy patio area with comfortable seating and a scenic view.

"Perfect accommodations for girls weekend. Close to everything, very walkable. "

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and ample cabinetry.

"We did a guys golf trip hitting courses around both Baltimore and Washington DC. We didn’t spend much time at the property but plenty of rooms and beds and perfect to get a few families together and meet up for a vacation"

CA $1,389 total

includes taxes & fees

Aug 11 - Aug 12

"Tracy's place was perfect for our trip to Annapolis. The home is very comfortable, clean and quiet. Tracy has the home very well stocked with all your basic necessities. We were able to walk everywhere we went with some great restaurants and shops very close by. We will definitely look into booking here again when we visit Annapolis."

CA $654 total

includes taxes & fees

Aug 25 - Aug 26