Holiday rentals with beach access in Chesapeake Ranch Estates-Drum Point

Lovely place to stay. Beautiful view, very peaceful. Sitting on the dock and watching the sunset became a favorite past time. Mary was so kind to allow us to use her patio to have my son over for food and games. It was a truly lovely stay. More amenities than any place I'd been to before. My only note was that the curtains in the primary bedroom are just sheer cloth, so the sun comes in at 5 am to wake you up, but that can be remedied with a mask, and changing in the bathroom was fine for me. The view is mostly wooded, so I wasn't concerned much about people seeing in, but I wasn't comfortable changing at night with the light on. The other thing to note is that the bedroom door does not lock from the outside, and there is access to the downstairs apartment from the house upstairs. It did not bother me, I took my purse when I left and didn't have anything to lock up anyway. Honestly this is a 5 star place to stay, and the little things are just that.

This is our second time staying at this cozy and tranquil retreat—and it won’t be our last. We first came here six months ago for a quiet getaway from the kids, and we liked it so much we knew we’d be back. This time was just as wonderful. The place is spotless, peaceful, and incredibly relaxing. The view of the bay is absolutely stunning—calm, quiet, and the perfect backdrop for unwinding. The hosts are warm and welcoming, and the space has everything you need for a comfortable and refreshing stay. If you’re looking for a serene escape with beautiful scenery and thoughtful touches, this is the place. We’re already planning our next visit.

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.

Great place with fantastic views of the Potomac . Close to many dining options within walking distance. We went for a Memorial Day weekend and had a great time. I highly recommend.

Sherril’s Bayside Oasis is an absolutely beautiful studio apt!!! It was spotless, comfy, and uniquely decorated. The location is convenient to the beach and within walking distance to plenty of shops and great restaurants and bars. Everything was smooth from check-in to departure. We had a wonderful stay and will most definitely check the availability of this rental when we visit North Beach again.

We had such a fantastic time at Maria's place! The instructions were clear, the house was beautiful and as described and the location was great! Maria was also a very responsive and helpful host! We will definitely recommend this place to others and come back in the future.

Sheila was a great host! She greeted us upon arrival, and left lots of helpful signage and instructions around the place, along with many recommendations for local restaurants and things to do during our stay. Gerry was also very friendly! This location was the cleanest airBNB we have ever stayed at. Although our stay was short, we had a great one! Check in and check out were also very easy. We would definitely stay at Sheila’s location again! It gave us the perfect location to do some fossil hunting and see some of Maryland’s beaches, and whenever we feel like doing more of that, we will be back!

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

A great stay on the river. The kitchen was well equipped and the rest of the house was comfortable. The screened in porch and access to the dock/beach/river was our favorite part. Our dogs were in HEAVEN. The location is rather remote, so recommend bringing any food you'll want as there are no close stores or restaurants.

This was our second time staying at Kimberly’s home, and it was just as magical as we remembered. The views of the water are absolutely stunning—whether you’re enjoying your morning coffee or winding down in the evening, it’s hard to look away. The location is perfect: peaceful but just a short walk to shops and restaurants. We also really appreciated the Peloton and treadmill—such a bonus for staying active during our trip. Everything was spotless and thoughtfully prepared. Honestly, we didn’t want to leave. Already looking forward to our next visit!

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!

Wonderful place - pictures do not do it justice. Home is spotless and beautifully furnished! We had a great time relaxing on our babymoon. Lots of great restaurants close by and so much to do at the house you never have to leave. Really appreciated the details such as the coloring station and ample beach towels. Hope to stay again in the future!

We had a lovely stay in Shark Tooth Cottage! We enjoyed the close proximity to the beach. The home was well equipped with everything we needed. Even things we didn’t expect like beach towels, toys and chairs. We will definitely be back for more beach treasures!

We had a wonderful time at Katerina’s place. Everything went well from check-in to check-out. Gus and Katerina provided clear instructions and were responsive. The house was nicely decorated. The neighborhood was peaceful and friendly. Private access to local community beach was the cherry on the top.

We really enjoyed our stay here. It was relaxing and super chill.

This place worked wonders for our family vacation. the place is very new and updated with 2 full bathrooms that were clean and spacious for beach time and baths with kids. colonial beach is a hidden gem in a historic little town that seems as though at one point was hustling and bustling but isn't quite as popular as it once was but trying to come back. if your a family looking for a uncrowded beach and some activities to do in the area then this place is great! we actually read about this place being in the heart of historic downtown. only thing we would have loved to see with this place is some outdoor patio spot at the home directly to be able to sit outside together. the location does not really have any night life during the week, not even on 4th of July. we went out at 9 pm and the bar closed at 10 pm which seemed way too early for a Thursday and holiday and being on the beach.

After a little miscommunication on the arrival time, everything was at it should be or better. Great location, clean, responsive well worth it. Great experience and will be back regularly.

I had an amazing stay at Jen’s apartment! The space was exactly as described—clean, stylish, and super comfortable. The bed was cozy, the kitchen had everything we needed, and the little touches (like the kid’s Conner and lots of board games ) really made a difference. The location was perfect—close to everything but still peaceful at night. Communication with the host was smooth and fast, and they were incredibly helpful with local tips. I’d absolutely stay here again and highly recommend it to anyone visiting beautiful Cambridge!

We had a great stay at Jen's place! It was very spacious and comfortable, and walkable to downtown Cambridge which had plenty of restaurants and bars to explore. The beds were comfortable and the amenities were as described. Jen was a very responsive host and helped out with all our questions. She also offered lots of local recommendations in Cambridge and the surrounding area. I'd definitely recommend Jen's place if you find yourself in Cambridge, MD :)

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!

Oxford is my favorite place to visit on the Eastern shore and I love staying in this little place near the town park. it's so peaceful and close to everything. I love connecting with the locals I've met on my travels. I look forward to returning!

Condo was in a perfect location in North Beach area. Loved walking boardwalk and walked 5+ miles daily. Felt very safe in the area, everyone was so friendly. Mexican restaurant and Baia were fantastic. Very peaceful. Condo definitely worth the money. Host was very responsive and let us check in early and was quick to reply to any text questions. Loved the view!