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

Lovely, well-stocked home with spacious, very functional coming area. Cristin was very responsive!

Launched the brand new sailboat I designed and built at a nearby boatyard and took it out for a few days of sea-trials. Terri's place could not have been better situated for this. Boat yard and restaurants all within walking distance. Plenty of stores nearby for supplies, and fortunately not right next to the house; the neighborhood is awesome. House is great for two couples - plenty of room w/spacious bedrooms, nice kitchen with big dining table, comfy living room with a great view of the harbor.

Nice place, had an issue with the ac but they had issues resolved quickly.

Perfect weekend away! The home backed up to the Chesapeake Bay. The home was very relaxing. Would definitely stay again!

I had a wonderful stay at this beautiful house over looking the bay! The views all around the property were absolutely stunning, creating such a peaceful and relaxing atmosphere. I was on a work trip with several coworkers, and the house was incredibly comfortable and spacious —it truly felt like home. The space was clean, safe, and well-maintained, making it the perfect retreat after long workdays. The kitchen was fully stocked with everything needed to prepare a large family meal, which was a huge plus. Most importantly, our host was amazing—she was incredibly kind, attentive, and thoughtful, anticipating our needs before we even had to ask. I would absolutely stay here again and highly recommend this property to anyone looking for a serene and welcoming getaway. Thank you, for such a great experience!

Stacey was so welcoming and kind. I felt right at home and the kitchen and bathroom were stocked with everything I might need. Next time I come through Waldorf, this will be my first choice. :)

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.

Lovely spot. Beautiful views. Excellent kitchen and living space with really nice bedrooms. Slept six very comfortably. Would definitely return!

Jacqueline's place is amazing! It is close to the sea and you can take a walk to enjoy the beautify view. I booked this for my uncles from China to attend my wedding and Jacqueline made us feel welcomed and gave us a tour for the place. The place has everything we need and is sparklingly clean. The host is easy to reach and always respond to our question in seconds. Highly recommend this place if you want something affordable and nice in the area.

Fantastic place. Welcoming. They thought of everything and more. Linens. Coffee. Electric fireplace. Laundry with iron and board. Toiletries. Glorious fragrance. High ceilings for a basement! Can’t say enough nice things about the place inside and out. Coming back as soon as I can.

This review is for a second stay as my partner and I had such a great experience our first stay, we didn't even look for other spots when we had to arrange travel plans a second time. This place is such a great deal - you get way more than what one would expect at such a price. And the hosts are truly wonderful folks - super responsive, kind, warm, and helpful, immediately responding to inquiries as they arose. Thank you Denise for your hospitality. The space, amenities offered, and helpful communication on your end made this trip one of our best yet. We really couldn't have asked for a better experience.

We had an excellent stay! The place was absolutely charming - such a cute little spot right in the heart of all the Leonardtown happenings. We used to live in the area and were back for a family event, so it was really special to reexperience all the things we loved about living there. The space was super clean, tidy, and easy to get in and out of. The directions and guidebook were spot on, and overall communication was fantastic. Haley was incredibly responsive and accommodating - especially when I accidentally booked for the day after we actually arrived! She was understanding, accommodating, quick to reply, and made everything so easy. Would definitely stay here again on a future trip!

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!

amazingly, comfortable and convenient place within walking distance of everything you could want to do! Very well stocked kitchen and didn’t leave us wanting for anything, I’ll be looking for this place again if I come back to the area.

My son and I stayed for a few days for the state championships at St. Mary's College. Overall, the place was excellent—the bedroom was spacious, well-equipped, warm, and cozy. The kitchen was a good size and included a full-size refrigerator. I would definitely stay here again.