Search Vacation Homes in Deale

"The house was exactly as promised! We were very happy with the accommodations!"

"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"

"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!"

"The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!"

"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...

"Loved the house!"

"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...

"This was such a beautiful cottage with the most picturesque garden in the backyard. The pool was an added bonus! The house is very quaint, beautifully decorated, and well designed for maximum usage of the square footage. If you are tall, you may struggle a little with the downstairs bathroom though. It was a serene getaway but close to absolutely everything downtown Annapolis has to offer. You can literally walk to restaurants and attractions!"

"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!"

"Everything was perfect and the host was very kind! Would definitely recommend, especially for anyone staying in the area for a wedding."

"This home was beautiful and very accommodating for my guest and I. It was nice, cozy and clean and I didn’t need anything because she had it there. I will definitely book this again when I’m in the area. Thank you for your hospitality."

"Got to go fishing, kayaking, and swimming in the pool. Had a great time, views are wonderful and it’s a peaceful environment. 10/10 would stay again."

"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"

"We had a wonderful time, house was nice, clean, and perfect location for our fishing charter that was at 5am! However, the neighbors complained to owner saying we were too loud past 10pm. In order to be well rested for the 5am fishing charter we made sure to be in bed before 10pm, so we were confused as to what was meant by " too loud, too late"?"

"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"