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

Very nice place to stay for our trip. Host was in touch and responsive during our stay.

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

The River House was phenomenal, a beautifully furnished place with large riverfront lawn and private boat launch. Exceptionally clean and well-stocked with everything you could think of for a comfy stay (fluffy towels, extra paper products, cleaning supplies, blankets, tons of pillows). Kitchen is as beautiful as the photos, and amply stocked with everything from ziplocs to pyrex to measuring cups and baking tools. The kayaks and canoe were easy to access and use. Easy place to paddle in a calm and quiet tributary. Highly recommend Lindy’s seafood a mile away. Host has compiled a guidebook with lots of local business recs and info. You will not be disappointed with a stay at this awesome retreat.

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!

This was my second stay at this Airbnb, and it was just as fantastic as the first—if not better! Returning felt like coming back to a peaceful little retreat. The space remains just as charming, clean, and thoughtfully put together, with every detail designed for comfort and ease. This time around, I was able to fully enjoy the private outdoor patio, and it truly elevated the experience. Whether sipping coffee in the crisp morning air or winding down with a cocktail in the evening, it quickly became my favorite spot to relax. The hosts continue to go above and beyond—warm, responsive, and clearly dedicated to making every stay exceptional. I’m already looking forward to my next visit. Still highly recommend without hesitation!

I loved the area, calm neighborhood, the inside is big enough to host up to 9 people. She respond very quick, I have good time, I would recommend it to friends.

Anne is very thorough when checking on a guest. She wants people to feel comfortable and makes sure they understand how to operate the appliances in the home. She has a garden and doesn't mind sharing the fresh herbs and berries in them. Initially, I was bummed about the strict check-out time (out by 8:00 am), but due to a delay in the cleaning service's ability to arrive to clean the place, I was able to check out at 11:00 am. She was responsive to questions or concerns I had. Her home is immaculate! She explained the cleaning/sterilization process, so this is a great place to stay for people who suffer from allergies. The neighborhood is quiet, and you are within walking distance of a few restaurants, a grocery store, and some shops.

Stayed at Erin’s place for a night and wish it was longer! The room is steps away from the restaurant I met with my friends at. It is situated near all that Del Ray and the rest of Alexandria has to offer. In addition, the bed was quite comfortable and the suite itself is quite luxurious.

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 had a great stay. Location was perfect for us. Easy to get to DC and old town Alexandra was fantastic.

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.

Great, clean place right in the middle of everything you could possibly want to do in Old Town, and so close to DC for all the big things to see! Clean, pretty home, comfy beds, and a nice gathering space for family to decompress in the evening. We had a great weekend!

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!

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!

Clean. Parks and rec. Close to food.

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.