Holiday 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.

This house is amazing! So much space and the Master Bedroom is so wonderful. Everything was clean and the street was safe and quiet. We will absolutely look to book here again.

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.

Beautiful classy neighborhood, beautiful house. Split level house, no connection or access between the levels.

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.

This was our second stay at Beach Please and it was just as delightful as the first! The house was again squeaky clean, thoughtfully decorated and had plenty of room for our multi-generational family to spread out. Grandparents appreciated the first floor master bedroom and kiddos loved the game room, and the crafts and puzzles upstairs. The neighborhood is peaceful and cozy, with beautiful views in every direction. The addition of the acoustic guitar for songs by the firepit was a major plus, as our ten year old is a music lover and almost brought her own. We had a great stay and would recommend this AirBnB to anyone! Grab a week (or two) and don't think twice.

Fantastic host! She was extremely responsive and helpful. We’ll definitely stay here again during our next trip to D.C..

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!!!

This is one of the best places I've ever stayed. No need to leave the house for anything except food. We use DoorDash, after the first night there because there were plenty of amenities right there. The very impressive kitchen has all cooking utensils and appliances needed. The theater is nicely decorated with a popcorn machine which gives the full movie experience. The pool table and air hockey were so much fun. The Pack-Man game was already a blast, then to find out it has a ton of arcade games on the system made it even better. The meditation room was a highlight of our stay. You'll get relaxed as soon as you approach the doorway. The gym was yet another amenity that we were impressed by. You get a pretty good workout while reading the motivational quotes on the wall. We used the grill that's conveniently on the patio at the entrance. This was my husband's first Airbnb experience so it set the bar high. The hot tub was great with privacy. I'll try the beautiful pool next time.

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!

Great location, very clean, toast is responsive. Enjoyed my stay very much.

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 had a winter visit and despite it being freezing outside the house was nice and toasty and we appreciated the fast hot water for showering. No fenced yard for our dog but it's a nice area to walk around. Central location, close to restaurants. Would stay again.

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!

The photos are mirror images of the condo. The kitchen and bath are amply supplied with all the items needed, even to prepare meals if you choose. Accessibility features are a bonus when traveling with an individual with mobility issues. Locally, Portside Seafood was a welcome surprise with a delicious menu. It was the perfect place for my sister and me to have some downtime and recharge. Thank you for sharing your beautiful home.

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.

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

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

Christina facilitated an easy and smooth booking and stay experience, it was greatly appreciated! The place was exactly what we needed.

Excellent host, very communicative throughout the process. I’ve stayed at the Wyndham several times and this was easily the most pleasant reservation process I’ve had with them.