Vacation rentals with a kayak 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!

This home was perfect for our family weekend two adults, two teens and a tween. The house was spotless and very nicely decorated. Matt provided very thoughtful amenities including a welcome basket. The Tiki bar was very cool And fire pit area and peer were pie favorite hangout spot Would definitely come again!!!

Some girlfriends and I needed a quick getaway, but what was only a two-night trip, felt like a weeklong vacation thanks to Jen’s place. We had a group of five and we literally did not leave the house all weekend. Before checking in, I made a quick stop for some last-minute items at the local market, which was three minutes from the house. We staggered the use of the kayaks and were pleasantly surprised by all the wildlife around the island…bald eagles, great blue herons, swans, even otters in the meandering marsh area! Between the games and books provided, the kayaks and water access, the hot tub and spacious bedrooms, each of us got a perfect dose of adventure, relaxation and respite from our daily lives. Not to mention, Jen, who was extremely responsive and helpful. Never have I ever had such a dedicated host. We’ve already agreed to book this house again next year. The location, the house and the host are what make this Airbnb special and we can’t wait to come back!

Great house. Clean, clutter-free, and nicely furnished. Amazing hosts. Lovely location. Clear instructions. It was just a lovely time overall. Thanks so much for hosting us.

We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!

Where should we begin? Lucas and Heather were wonderful hosts. Excellent and quick communication. Their home has been thoughtfully curated with top notch, kitchen appliances, bed and bath linens, entertainment amenities, and more. Even on a cool and rainy day, you can sit around the fireplace, listen to music, play games and look out the window to a stunning view of the water. No stone was left unturned. This is indeed a special place in the lovely little town of Oxford. We hope to stay again. Thank you, Lucas and Heather for the exceptional hospitality.

This was our fourth time staying at this wonderful property, and it never disappoints! The house is clean, comfortable, and perfectly situated with beautiful views of the river. There is so much for kids to do — our ten-year-old twins stayed busy all day every day with the treehouse, slide, trampoline, swimming off the dock, tree swing, crab traps, and the many board games and puzzles provided. One of the things we love most about staying here is that there’s so much to keep the kids happily entertained, giving us parents time to relax by the firepit and truly unwind. The home is thoughtfully stocked with anything you might need, and Landon is always a pleasure to work with — friendly, responsive, and communicative. We already have our summer trip booked and can't wait to return!

Beautiful, relaxing, multi-family house right on the water. The outdoor space is huge and completely fenced in so our kids and dogs could run free safely. The house itself is full of things to do (karaoke machine, hot tub, ping pong, etc.), and is also really close to several state parks, beaches, and more. We will definitely be back!

Jessica and Richard were very welcoming and friendly. Place was great right on water. Very private. Grandson and I fished off dock with good success. J&R lent us a crab pot and we had a blast.

My husband, dog, and I enjoyed a wonderful Thanksgiving break at this very nice and beautifully situated cottage! The views from the back deck and kitchen are as gorgeous as the listing photos suggest and, while the house is right next door to another one, we heard not a peep from the neighbors during our 5 days there. Everything was very attractive and well thought out - the kitchen was well appointed with everything we needed; the chairs, sofa, and bed were super comfy, the bathroom was clean and cheerful. Maxine was great host, answering all our questions quickly and helpfully. It's a 15-20 minute drive to downtown Cambridge, where we had nice dinners out in town at Blue Ruin and Bombay Social. We also took good day trips to Easton, St. Michaels, the Blackwater National Wildlife Refuge, and the impressive Harriet Tubman Underground Railroad Park and Visitor Center. The whole area is full of beauty and history, and this cottage was a great home base!

Quiet and cozy home in the perfect location. We had a wonderful stay with beautiful views of the water (too cold in Feb to fully enjoy), and it was so convenient to be able to walk to local coffee shops and restaurants. Would definitely stay here again!

We loved our stay at KJ’s property and will absolutely be back again! The house was perfect for a weekend family getaway with beautiful views and lots of things to do at the property itself - you really never need to leave! Meticulously clean, great fire pit, lots of outdoor seating and an overall very private location. Would highly recommend to anyone looking for a relaxing experience!

Absolutely amazing host and home! This was our second stay at Kyli's listings and we will continue coming back. Super responsive and friendly, we felt completely comfortable and safe throughout our trip. The amount of outdoor amenities provided here made our spring break a memorable one. Would reccommend to anyone interested in having a 5 star trip!

Rachel’s place was Awesome! The water view, pier, fire pit and house made us feel at home. We were in town for a funeral and Rachel was very accommodating. With check in and check out. Our family grew up in piney point just a short distance away and we were able to reminisce and site see of the past. The ruddy duck restaurant on the island was a great place to gather after. Thanks again!!

Linda's cottage was absolutely beautiful. Her kitchen was fully stocked with all of the necessities we needed, and although we brought our own supplies, we never had to use any of it. Linda communicates very well and her instructions/requirements are easy to understand and follow. The cottage was spotless upon arrival. The view of the river was so pretty it provided us a moment in time to meditate and enjoy each other's presence with no interruptions. My husband truly enjoyed his birthday experience at Linda's cottage! That was all I could ask for. Thank you Linda for allowing our stay at your beautiful home ❤️

The cottage was a perfect place for a relaxing anniversary getaway. Beautiful views, peaceful setting. House is very well maintained, clean and comfortable. Easy to launch canoe /kayaks from the dock, campfire by the water watching the moonrise over the water. Perfect, would love to return. Highly recommend.

Just a stunning location! The bird watching was marvelous, every morning a pair of swans landed and swam around until dusk. Lots of blue herons, too. Good fishing right out of the back yard. The kitchen was very well appointed, good cookware, plates, cups, etc. bed were comfortable with really nice pillows. We spent most of our time around the fire pit or on the screened porch. A great place for relaxing!

This was our second time staying at Julie's lakeside cabin and it was wonderful again. Modern, tidy and very comfortable rooms and beds. The amenities are fantastic - we loved the arcade and watching wildlife around the pond (saw bald eagles, osprey, and even a snapping turtle! - the hot tub was a great way to relax and warm up after a day at the beach. Convenient short drive to several beaches to comb for fossils - lots of good places to eat in and on the way to Solomons. Julie is a great host and a great communicator too!

Awesome little cabin. Very clean, really comfy beds and a great log cabin vibe. Keyless entry is easy to use and cabin was well stocked with necessities. Beaches nearby are really fun to walk. Water in the bathrooms, sink & outside hose did have a sulfur like smell to them but the host confirmed it was a new well & water filter likely being broken in

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.

Lovely and quiet stay! We wanted to get away from the city for a few days and this was exactly what we needed. The house and lake are beautiful, clean and quiet.

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.

This was our second time staying at this cute place. We knew what to expect; took all linens, pillows, towels, kitchen towels, etc. as she lists. Also took two door mats and non-skid mats for the showers (the master shower was quite slippery so I knew to bring a non-skid mat). The place was pristine, from the kitchen to the bathrooms. The floors were spotless. Landscaping is mature and nice. The little beach was perfect for us -- while it is not private, and anyone can use it, during the two times we have visited, spring and fall, during the off season, there were only a couple of folks who walked; nobody set up chairs; we had it to ourselves. I imagine during the summer that is not the case. Liezel is delightful to deal with, friendly, responsive, concerned. We love her little funky log house, and will definitely return! Thank you Leizel!