Search Holiday Homes in Chesapeake Beach

"The stay was a perfect location for doing things in downtown St. Michael's, everything is within walking distance. The property managers were prompt with all communications and pleasant to work with on a few questions I had."

"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...

"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."

"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!"

"My husband and I moved from the area two years ago and so are in town frequently to visit friends and family. Weve stayed at the Lazy Crab and the owner's other property next door at the Blue Crab multiple times. The properties are located in a quiet neighborhood within easy walking distance of restaurants and shopping, and plenty of parking is provided. The houses are well appointed and provisioned, nicely decorated and comfortable, and always beautifully clean. Danielle is very easy to work...

"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."

"Very warm welcoming home, the environment surrounding the property is mesmerizing! Host was very friendly and understanding. Thank you for allowing me to have a good bday weekend!"

"Great place for a short moms getaway. Walking distances to many things. Heard live music from the porch. House is spacious and extremely clean"

"We booked a long weekend for our daughter’s graduation from St Mary’s. The house was beautiful and so spacious for our adult children and grandchildren to all be in one location without feeling cramped. We loved having the fire pit and room to throw a football around. Thank you for sharing your home Victoria!"

"If you have a big group this is the place for you! We had a great time!!"

"The house was in the perfect locatfor us and our two dogs. Tammy was always available to answer our questions, very approachable and professional. We highly recommend this property to anyone."

"Great location and house! We all had a great time!"

"Nice and super clean. Nice location. We will stay again next time we visit family. "

"Beautiful house. Great location. Host was very responsive to questions. Thanks for a great stay"

"Very comfortable and quite meet the owner and very nice will stay again"

"The house was clean and quiet. The hosts were helpful and available for communication. This is a lovely house for a vacation away from crowds and by the beach."

"The house was lovely. We had 3 days of rain but the view and the beach made it interesting at all times. The hosts make sure you have everything you need for your comfort and entertainment. This is by far the best appointed house we have rented. Thank you for a wonderful week!"

"Everyone really loved the house and the location. The pool was great"