Search Vacation Homes in Annapolis

"The property was beautiful. The property manager was available for any inquiries we had. My family and I enjoyed it immensely. The view of the water was wonderful whether sitting on the dock or sitting in the sunroom. We played indoor and outdoor games. Perfect place for family bonding. The weather was perfect for our stay."

"Great location for commissioning week! The house was cute, cozy, clean and we loved it!"

"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."

"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"

"I stayed at this property for a family wedding this last weekend with 5 other adult family members. The original spot we booked fell through last second and I found this unique property. It fit our needs perfectly. There was plenty of space. Everything was clean. The outdoor sitting areas were an added bonus. Plenty of parking. And the location in relation to downtown were perfect. I’d definitely stay here again."

"Super close to all downtown amenities. Would definitely return."

"This top floor apartment appeared to be recently updated and was immaculately clean. The hosts thought of all the little extras that make a short term rental special. It's located in the heart of annapolis and is easily walkable to soooo many good restaurants and bars. Beds were comfy! The kitchen has some awkwardly angled ceilings, so tall people will need to duck down, but as long as you aren't walking through looking at your phone (like I was), it's totally not a big deal. Even though it is...

"This home has a fenced-in backyard and is dog-friendly, making it a good spot for visiting Annapolis with a dog in tow. Along with being a five-minute drive to downtown Annapolis, this home is also close to Quiet Waters Park. Sean is terrific at communicating; the complimentary wine and coffee were appreciated!"

"Small but mighty Eastport house, super convenient to all thing Annapolis. Clean, equipped, comfortable. Mark is great at all things communication. Stay here….just not on the dates that I need it!"

"Our stay in Annapolis was a short and sweet 3-day visit for a wedding--my original focus was to have enough space for everyone to get ready without waiting in line. The property provided so much more than enough room. The entire house was very clean, well-appointed, and smartly laid out. The kitchen was stock with a wide range of food to get the weekend started off without the need to spend hours in the local grocery store. Throw in a great ping-pong table to make it even more fun. My only two...

"421 Irie was the perfect perch in Annapolis for our son's wedding weekend, exceeding all of our expectations. Liz made us feel incredibly welcome from the moment we booked with her lightning-quick responses, warm hospitality, and thoughtful personal touches. The home was immaculate and had every amenity we could have wished for. Its convenient location made it easy for us to navigate to and from wedding events, while the comfort and coziness of the house made it the ideal place to relax and...

"Our stay in Oyster Harbor was very nice. The weather didn't cooperate but the house itself was very nice and I would certainly stay there again. It's about a 10 minute drive to downtown Annapolis so that made it convenient as well!"

"We had a family reunion in Annapolis so we booked all three units. It was Thanksgiving week and we came from the West Coast. It has a large wonderful yard with lots of amenities to include a fire pit, gas plumbed and a grill. It is close to everything downtown yet not too close. We had everything we needed to have a Thanksgiving meal for our family. The hosts were helpful, responsive and amazing. It has super cute decor and felt very comfortable and cozy. I would highly recommend a stay here."

"This property was as advertised. Close walk to stadium but too far to walk to USNA campus for us."

"The house was super cute and the host was great!"

"We were in town for a wedding, and this house was a wonderful place to stay for the festivities. There were 4 adults in our group. We were hardly at the house, so didn’t get to take advantage of some amenities. Beds were very comfortable, towels were large, soft, and plentiful. The house was well appointed and very clean. Only drawbacks were the small size of the downstairs bathroom, and distance to the parking garage. If you don’t need your car at all while in town, it’s not a big deal. If...

"Wonderful place to stay! Close to everything. Parking was a big bonus. Host responsive with our question. Will rent again for our next Annapolis visit."

"Absolutely enjoyed our stay. Wonderful access to the Yard and DTA. Home is clean, well equipped, and very functional."