Vacation rentals with outdoor seating in Chesapeake Ranch Estates-Drum Point

Michael's place was perfect for our spring break getaway. I really liked the laid back beach vibe and how kid friendly the house was. The kids were able to walk to beach themselves and had a great time on the trampoline! We loved seeing who could find the most shark teeth.

The house was amazing. Very spacious and cozy. The description of the house is very on point. There were even Christmas decorations up which added ambiance considering we traveled there for Christmas. We did have to move a few out of harms way(the little kids), but all in all the decorations added flair to the space. There wasn’t much interaction, because everything was great. But we were kept informed of the necessary information.

I’ve stayed at a lot of Airbnb’s and this was easily one of the best. Everything was exactly as described, and maybe even better than described. It had tons of amenities and a well stocked kitchen perfect for our large family. Spotless and beautiful. I highly recommend this home and would gladly stay there again.

We had an amazing stay at this riverside house! The views were absolutely breathtaking, especially at sunrise and sunset. The house was clean, cozy, and well-equipped with everything we needed for a comfortable stay. Being so close to the water made it feel like a peaceful retreat. Highly recommend for anyone looking to relax and enjoy nature!

This house is perfect for large groups. It is very spacious, with plenty of room to spread out and get comfortable. We enjoyed sitting on the dock taking in the serene natural beauty of the Creek and observing the local birdlife, including Kingfishers, Great Blue Herons, and Bald Eagles. The house is situated very near to the entrance of Lookout Point State Park which we greatly enjoyed exploring on bicycles. Seeing a large wedge of Tundra Swans fly overhead was a special moment. If you want to spend some time relaxing in a beautiful setting in a beautiful and very interesting area with a large group, this house will serve you well.

Great, Kid friendly, Family oriented. Host is kind and extremely involved and responsive. This will be added to my favorites ❤️

This home was perfect for 6 of us to stay. The beds were comfortable, the heat & AC worked perfectly for the fluctuating temps, the kitchen was well stocked, and there was great space both upstairs and down. I’d definitely stay here again!

I can’t say enough wonderful things about Melissa’s place. As soon as you walk in, you feel right at home. She has thought of every possible thing you could need while there. The views were absolutely magnificent and while the beach area is available to the public, it felt super private. My daughters and I plan to come here every year. I had to peel them away from the bay. Melissa, thank you for accommodating us. This was a weekend my girls and I desperate needed and your home was the perfect place to have peace and intentional quality time. Thank you so much!!

Ms. Marcea was an excellent host! She checked on me to make sure I had everything I needed throughout my stay. Being here for a month, she would occasionally drop off some goodie bags, fruits and veggies and a sweet treat!! I work nights and had NO trouble sleeping. The house is quiet, the apartment is private, and I would certainly come back and stay! Thanks so much, Marcea!!!

Very quiet and peaceful home. Jennifer was very helpful and extremely responsive. The home was very clean and spacious, they provide plenty of activities for your entertainment or it’s extremely easy to watch a movie and just relax. The home was exactly like the pictures, check in and out was very easy.

This place was great to visit DC, and a much cheaper alternative to a hotel. We arrived very late and she was very accommodating. would recommend!

We could not be more pleased! The property was beautiful, clean, and spacious. Don’t let the fact that it’s above a restaurant fool you. The ceilings are high, there is ample space and privacy, and the layout and decor is superb. But the best part of our visit was the incredibly responsive host who answered our questions (even if they were silly) and clearly wanted to ensure our comfort. We will love to come back and are already recommending this rental to friends and family!

Exactly what I wanted. A comfortable, cozy, quiet getaway, walkable to phenomenal scenery and restaurants. Loved it.

What a calm and peaceful private retreat! My fiancée and I spent a couple of days enjoying the brisk bay breezes and beautiful sunsets at Vickie’s. Everything was exactly as advertised and Vickie (and Scott) are true treasures—extremely responsive and thoughtful hosts who want you to have everything you need. Plus, their knowledge of the area gave us a great introduction to Leonardtown. So much more to the area than we thought! Whether birdwatching from “the best view on the block” or reflecting on the glider by the bay, we loved every moment of quiet and can’t wait to visit again. Thank you!

The location was beautiful and the home was very cozy. Sitting on the screened porch, reading and enjoying the view of the yard and water was good for the soul. It was very quiet and we had all the amenities we needed.

We spent a month in this apartment while waiting for our new home, and we couldn’t have asked for a better experience. From the moment we arrived, everything was perfect—the apartment was spotless, beautifully furnished, and had all the amenities we needed to feel right at home. It was spacious, comfortable, and an absolute pleasure to stay in. What truly made this experience exceptional was the hosts. They were beyond amazing—thoughtful, responsive, and genuinely committed to making sure we had everything we needed. When we had an issue with the refrigerator, they didn’t just fix it; they replaced it with a brand-new one within two days! Their kindness and efficiency made us feel incredibly valued as guests. Spending a full month here, we truly got to appreciate how well-maintained and well-equipped the apartment was. It was a perfect home away from home, and we are so grateful for the hospitality we received. We highly recommend this place to anyone looking for a fantastic stay!

Our visit is always wonderful not only for the lovely setting and convenience of being in town, but for the gracious hospitality. Not only are Chris and Kate welcoming and attend to any needs, their staff at the Oxford Market are also marvelous folks. The cottage is a great fit for my elderly parents as it is all on one floor. The location is perfect as you can walk to many delightful places. My Dad enjoyed getting the newspaper and homemade muffins each morning. Just perfect! Thank you! Katie Dodds

This home was clean, and there was plenty of room. The outdoor space was excellent. The host communicated well and responded quickly. We had no issues.

Our stay at this Airbnb was absolutely wonderful. The location is fantastic right on the water across from the small beach that is available and right on the boardwalk. We used this for a getaway with my wife, and we spent a lot of time just sitting on the balcony people watching and enjoying the beautiful view of the water. The owners were very responsive answering questions and the instructions to get in were very easy. We were walking distance from anywhere you would like to go- restaurants, Café, ice cream, the boardwalk, and the small beach on the bay right across the street. We were also a very short car ride or a bike ride away from another boardwalk on the bay and the Chesapeake beach Railway Trail through the marshes. The condo was very clean and well equipped. Decorations were lovely and everything felt brand new and spacious. There were two bedrooms and while we didn’t use one of them, the bed that we slept in very comfortable. We definitely recommend!

House was great with space for everyone whether we gathered for a meal or game wanted to spread out. Super easy walk to the beach and boardwalk. GREAT coffee shop and a few gems of restaurants and shops-we were definitely there in off season and the town was not fully opened - lots of opportunity in the town and lots of places getting opened for the season! Would be a great place for a quick summer getaway