Vacation rentals in Chesapeake Ranch Estates-Drum Point

Such a beautiful location with a wonderful view, I came for a staycation just for the night and it was absolutely worth it and exactly what I was looking for. I can’t wait to come back in the warmer months!

Perfect Stay in Deale, MD I had a fantastic stay at this beautiful waterfront home on Carr’s Creek. The hosts were incredibly attentive and made sure I was comfortable the entire time. We had snow during my stay, and they had the driveway and sidewalks cleared almost immediately after it stopped—such a thoughtful touch! The views here are stunning—pictures don’t do this place justice. It’s peaceful, quiet, and in a friendly neighborhood where I felt completely safe. It’s also super convenient, close to great food and anything else you might need. The house felt like home—spacious, welcoming, and fully stocked, especially the fantastic kitchen. Whether cooking, bird watching, soaking in the hot tub, or taking in the view, it was the perfect getaway. If you’re looking for a peaceful escape with family or loved ones, I can’t recommend this place enough!

Perfect location for a quiet, relaxing getaway. Everything about the stay was perfect and exactly as described/expected. We alternated between cooking in the AMAZING kitchen and eating at host recommended restaurants in North Beach. The house is located close enough to town if you choose to eat out (barely 5 minutes) and an acceptable drive to major grocery stores (15 minutes) if you opt to cook a few meals. The house was spotless. Hosts are super responsive and incredibly nice. Highly recommend staying at Bell Estates. Thank you, Daniel, for the perfect long weekend with my family!

This cabin was everything we wanted and more! It’s in the perfect location, just a short drive to so many activities but also tucked away offering privacy. The house was so cozy it put us at ease as soon as we walked in. The owner was proactive and very quick to respond, including sending a great packing and local activity list a couple days in advance of our trip which came in very handy. Activities: This rental comes with guest passes to the private Shark Tooth Beach where our kids had so much fun finding real shark and manta ray teeth in the sand! Westmorland State Park and George Washington’s Birthplace both had great hiking and beaches for the kids. We visited Garners Produce twice where the kids fed animals and pedaled toy tractor’s while we picked up farm fresh milk and eggs. We spent our afternoons kayaking on the quiet lake soaking up the sunshine. We will definitely book another vacation at this cabin. You will not be disappointed with your stay at this little gem!

It’s super cute, quaint and has such character. Something for the whole family we will be back.

Cheryl’s stay was so peaceful, comfortable and fun — even before pool season started. We could not believe how large the yard was and how quiet it was. Amazing wildlife. We saw bald eagles, heron, geese and lots of ducks! The house was squeaky clean and had everything we needed. We watched the stars at night and slept soundly. Downtown St. Michael’s is only about 10 minutes away and full of fun things to do. We’re so happy to be acquainted with the area after staying at Cheryl’s!

We thoroughly enjoyed our stay at this AIRBNB. It was walking distance to a nice Mexican Restaurant as well as to a brewery. We spent hours on the front porch in the nice rocking chairs. The back of the property overlooked the water which was beautiful! It was close to everything in town! The house was clean and had all of the necessities. We also enjoyed the front sitting area during the morning. The owner was responsive and helpful! We would definitely recommend this property.

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.

We were 4 adults and 1 child (9y). We absolutely loved our stay at Jackie’s place. She was proactive in her communication and very flexible. She was able to offer as an extra night for free. We understand that this will not always be possible but it isn’t the norm nowadays anymore and it shows she goes above and beyond for her customers. The house was close to the beach, clean and everything was just as described online. We loved the quiet area, perfect for families with children or people who don’t like overcrowded beaches. Our boy loved catching jelly fish, collecting rocks and shells and of course being in the water. Our favorite restaurant was high tides (yummy cocktails and the best fish and chips basket). We also ventured out to see James Monroe’s and George Washington’s birthplace which were only a 20 minutes drive away and really worth a visit. Jackie, thank you for everything!