Vacation rentals with a firepit in Chesapeake Ranch Estates-Drum Point

I don’t know if I can express how much I loved our stay at Rich and Yumi’s place. The property is very beautiful, private and very peaceful. We enjoyed fishing and taking in all of the sights and sounds of nature surrounding us. The fire pit area and hot tub were very nice additions to the property. The house was very clean and comfortable. The house was very well stocked. Rich and Yumi pay great attention to detail. We were greeted by a nice welcome basket and card to welcome us. After departing we realized that my daughter had forgotten a few items. Rich was very responsive and helpful in locating the items and arranging to ship them to us. I absolutely fell in love with this place and definitely plan to return in the future. Thank you very much Rich and Yumi for sharing your amazing property with us!

Enjoyed the stay!

Our stay in North Beach was lovely! This was the perfect getaway for us, our 11-month old baby, and our dog. The house came equipped with all features as-advertised, including the hot tub, Peloton equipment, and coffee gear (all of which we used). Our dog loved the sunny lookouts, and our baby loved crawling and climbing the many stairs. (The house was extremely clean, and we had no qualms letting the baby crawl everywhere.) Kim and Scott were especially responsive; there was a brief issue the night we arrived, and they were right over to fix it in-person. We will definitely be back!

Another great stay with a wonderful host in a lovely house on the water.

We had the best time at this house!! Gorgeous view and the pool was perfect. The house had everything we needed and it was very comfortable for our family. We cannot wait to come back next summer!

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 the pleasure of staying here during the winter while we looked for a place to live. It was perfect! Quiet and peaceful yet super close to all restaurants and stores. We had some snowfall and the views were stunning! Once it warmed up we even got to see some wild life in the woods behind us. Lovely huge porch! Lots of space in garden escape. Can bring the entire family and more!!! Nice big driveway for easy turned around. Patrick was beyond responsive for all my questions.Whether is was just informing be as something as simple as an Internet outage in the area or we had one situation with an unsure smell. Patrick acted immediately on the problem and it was resolved within 2 hours from start to finish. Cannot recommend this place enough!

thanks so much for the lovely stay. I thought it was so sweet they reached out to ask if it was okay to do some light decorations for christmas. I appreciate the consideration and loved them. when I arrived at the home one of the smoke detectors was chirping and I offered to replace it if they could tell me where some batteries were. bill came over right away and took care of the chirping detector. I really appreciate that.

Jennifer was an awesome host! Loved the space and we had an excellent time. Would definitely recommend!

So very peaceful. Loved watching the birds fly off an on to the neighboring pier. Fit our needs perfectly and with the well stocked kitchen we were able to prepare our Thanksgiving meal.

We stayed at Maria’s place while visiting our wedding venue (Herrington on the Bay) for a tasting! It was super close and convenient, especially since we have 2 small pups and love brining them with us :) Maria was extremely helpful with recommendations for restaurants close by, and her place was cute, quaint, and well stocked. We felt very much at home! She was also flexible with allowing us to check in a couple hours early so we could drop off our stuff and the pups before heading to the tasting, which really helped us out. And the back yard area was perfect to let the pups run around and get out some energy. We will definitely be recommending Maria’s place for vacationers and future wedding guests! Thanks again!

Dave and Karen are wonderful. Everything about our stay was excellent. I would highly recommend this to everyone.

Mary was a great host! House is in beautiful location and right next to the waterfront. Wish we had more time to stay! Would love to go back again in summer

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!

This was a perfect spot for a short getaway from DC. Shawn was very responsive and helpful throughout our stay. We would definitely love to come back!

We had a great stay. This place is tucked away and private, but also close to the action- plenty of restaurants, bars, and recreation. Park your car and walk everywhere. Don’t be afraid to bring your dog. This is a great spot for having adventures with your pup or for leaving them in the apartment for a bit. Space was clean and comfortable. Hosts were proactive and accommodating. We hope to come back.

Our favorite spot to visit and recommend it enough. Always feel right home and relaxed as soon as you walk in the door

We absolutely loved our stay at Cinthia’s cabin. Everything about the home was so beautiful. Very quiet and peaceful surrounding. Didn’t have any trouble getting around. The rest of the ladies enjoyed the cabin as well. I would absolutely book and recommend this space to anyone!

We loved our experience at John’s cabin! It was so incredibly peaceful - our host could not have been more friendly & helpful, even on a holiday weekend, the woods were beautiful surrounding the lovely cabin on a hill, and the beds were comfy. We definitely wished we were staying longer than a weekend!

The weather blessed us with warmth upon arrival to Pizza Friday. Although making pizza was a new skill we gained in the moment, the fun we had while doing it was everything we wanted. We had a chance to use the fire pit, kayaks and games in the house. The kids enjoyed sleeping in tents on the ground and the Easter egg hunt scattered along the lovely property. The host was super responsive and allowed us to check in early at no additional cost. I think I may have messaged him a few times about AC and fire wood and there was no hesitation on getting back to me. The family loved this Airbnb and we have already planned an additional trip in the future.

I recently had the pleasure of staying at Alexander and his wife's charming cottage, and we couldn't be happier with the experience. From the moment we arrived, Alex and his wife were incredibly accommodating and helpful, ensuring we had everything needed for a comfortable stay. The cottage itself was cozy and well-maintained, offering everything we required for a relaxing getaway. One of the highlights of our stay was the breathtaking sunset views. Watching the sun dip below the horizon from the dock was simply mesmerizing. The location is also ideal—just a short 10-minute drive to downtown St. Michaels, where we enjoyed exploring the local shops and restaurants. The hosts truly go above and beyond to make their guests feel welcome, and it shows in every aspect of their hospitality. I highly recommend this place for anyone looking for a peaceful and memorable retreat.

A fair and open spaced home. Free of clutter. Many updated electronics I didn't expect. Only drawback was the microwave. It had a lagging door switch that locked when it was ready. If your impatience, it would test your nerves. A shower that was plenty hot and spacious. Loved the size of the home and location, I want to rent this again.

We absolutely loved staying in this beautiful air b n b! The scenery was outstanding and was definitely one of the most peaceful stays we have experienced! We will 100% be booking again in the near future!