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

Very roomy for a family vacation. Great location and covered porch was great for taking in views of river and enjoying summer breeze. Host was responsive and provided detailed instructions.

We loved the experience from booking to check-out. The setting exceeded our expectations. Peaceful and beautiful landscape. Easy to launch kayaks. Chickens were an added bonus. Appreciated the close proximity of Blackwater. Would love to return.

The house was super cute! We stayed for race weekend and it was perfect - quiet, on the bike route and close enough to town to not feel rushed getting back and forth. Rebecca’s house might have the cleanest floors I’ve seen in a rental and the kitchen had everything we needed. Race logistics can be stressful and it was wonderful to have an affordable place with plenty of room and no noise.

What a find! We were attending a wedding on the Potomac and found this gem of a place basically right next door. A perfectly appointed home in a peaceful, tranquil, beautiful setting. Connie was great! Responsive to our need to find the iron, not exactly an emergency, Connie responded immediately with it's location. Loved it!

We visited Southern Maryland for a family wedding. The property is beautiful and peaceful. Beds are comfy, house comfy, and they thought of the little things like : a full sized ironing board & Iron, beach towels, good soaps, and all you need for s’mores!Their welcome handbook was very detailed. Our only regret was that we could not spend more time on the property itself (because of family events). Would have loved to use the kayaks and the fire pit. My brother did use hot tub. Great stay! Highly recommend

Edna’s place was perfect for my sister and I visiting relatives that live in Lusby. The property is beautifully updated and extremely comfortable! Edna checked in to ensure all was to our liking. Everything you can think of was there for a meal preparation and then some. Next time I back I truly hope this place is available!

The venue, property and service made great memories. Our host went above and beyond to help and especially with a special request that only an exceptional person would do. We had a wonderful stay and look forward to another visit.

My family and I stayed here for a week for our family vacation. We are a group of 8 (6 adults and 2 kids) and there was plenty of room for all of us. We barely left the house because with the beautiful view, dock, beach area, canoe, kayaks, hot tub, game room/ library, corn hole, and fire pit we all had plenty to keep us entertained. Everyone loved Mary & Shelly’s place, and it provided the perfect space for us to enjoy the river and each other’s company!

This is a great place to stay and tour the DC Metro area - provided you have a car. Most days it would take us 30 minutes to get to and from DC though if we hit rush-hour, it was as long as an hour. The space is tidy and great. My kids love the pool, though it was a little cold for me-they swam there every night. Jennifer is great to communicate if you have any needs she gets stuff done right away. Note that there is only one bathroom, which can be a pain if you have a full house of six people. The washer and dryer are small so it will take you longer if you’re used to a full size. She had all the cooking methods and appliances available. The theater room has Netflix and Amazon prime ready for you to watch a show. There is even a popcorn maker. We did not use the gym, but it was nice - comparable to a small hotel gym. Property is in the owner’s basement, so there is some sound from upstairs as identified in the listing. Host stays out of your way but is there if you need anything.

We enjoyed our stay! Easy drive to Alexandria, Georgetown, and all DC attractions. Home was comfortable and exactly as described.

Autumn and her brother went above and beyond in our stay. My friends and I felt right at home the moment we walked in and appreciate how helpful you were. We will definitely be booking here again. We love the backyard lol.

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!

We rented A Little Slice of Cambridge because of the Iron Man competition held that weekend. It was convenient to the venue...and allowed to walk to the competition and nearby restaurants. Pamela was a wonderful host...communicating easily. The rental was well stocked with toiletries, dishes, pots and pans and extras. The house was comfy and the beds comfortable. An enjoyable stay...unfortunately, we weren't able to stay for more sightseeing...although I did walk down to the Lighthouse and beautiful wharf.

Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.

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!

Place was nice and in a good location. Host was responsive. Good news is that it’s in a good location, but it is by the main road and can get a little loud, probably mostly on weekend nights. But places close early, so noise doesn’t last long..

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.

Brandon’s home was as beautiful as the pictures. We loved how easy it was to walk to everything in the town. The pool and rooftop patio were an added bonus. We enjoyed cooking in the large kitchen, and the house easily accommodated our group of 8. We will be back!

Suite Life's, was great my family and l had a blessed and wonderful time, the beds where so comfortable we over slept. lt is a great place for anyone especially family. The host made everything so nice and convenient from check in, to check out.

I lucked into David's place while attending a conference in National Harbor. The two-bedroom apartment was large, recently refurbished and more than met my needs. It was extremely convenient to the convention center. The staff at the resort were helpful and pleasant and the jacuzzi tub in the apartment --and lovely outdoor jacuzzi in the main resort-- ended up being a treat as well as a blessing for my sore back. The price is high but so are all the hotel prices in the area plus the apartment is big and there were amenities at the Club Wyndham that you don't get at other places. Would stay again if I have to return for another conference

Chris was a great host making check in and out so easy and flexible! The location of the place was perfect for walking to the market and to get coffee! The space was exactly like the pictures and perfect for a quick getaway with my fiance! Recommend this place!

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

I was upgraded to a 2 bd 2 bath suite and it was amazing! We didn’t need all the space as it was just 2 adults and a toddler but it was still very much appreciated for the price paid. The area is perfect with lots of restaurants, the harbor a short walk away and many other easily accessible activities. This is a timeshare resort, if you’re not interested in the presentation just say no but expect that you will be solicited. The resort had so many wonderful accommodations and is so kid friendly. The only complaint I had was that one of the bathroom sinks clearly hadn’t been cleaned which I found odd because everything else seemed pristine so I didn’t make much of a fuss about it just cleaned it myself. I would definitely return.