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

We had such a wonderful stay! The kitchen was incredibly well stocked—honestly better than my own at home—with 5-6 large pots, an Instant Pot, every spice you could think of,peelers (which saved me!), and both a NutriBullet and a regular blender. It made cooking for the family a breeze. The kid had a blast on the trampoline, and we all loved the easy beach access with calm waters perfect for swimming all day and kayaking. The beach was also perfect for a peaceful morning run, and at night we could see the lighthouse light on the water. The porch quickly became our favorite spot—we gathered there to watch a rainstorm and were treated to a stunning double rainbow. The sky was full of stars at night, creating such a peaceful atmosphere. The grill on the porch made cooking super convenient. We enjoyed being close to a large park where we played pickleball. The beds were large and comfortable—everyone slept really well. Michael was a fantastic host—very attentive and accommodating.

The hosts were amazing and responsive, and the house was beautiful! I would definitely stay at this home again!

The location is peaceful, private and gorgeous. It is as just what I wanted and needed for my 50th girls getaway! We loved every second there! The beds were comfy, location was quiet, the water and outdoor amenities were perfect! We easily made it work for 6 girls and one bathroom- which was no issue at all! A storm came through and left us a beautiful double rainbow! There is a resident bunny who comes out mornings to forage. We spent most of our time relaxing by the water with the chairs, loungers and umbrellas! My daughter and her friend played safely and happily on the shore by the water and my friend and I kayaked over by the cliffs. It was a perfect weekend at Colin’s and we plan to come back again! What fun and relaxation we had in a private setting with very nice neighbors. It went BEYOND our expectations! Colin was always kind and super timely when responding to any needs. We will be back! 💓🙌🏼

The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!

The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.

This served as a low key weekend retreat for us. We unplugged and enjoyed being in each other’s company. Being on the river, surrounded by trees and birdwatching was exactly what we needed. The kitchen was well appointed so we were able to enjoy family favorite activities (cooking together and playing board games).

We had a very enjoyable stay at this perfect River House. The place was warm and comforting, with some of the most amazing views you can find. We arrived shortly after check in time, and easily let ourselves in with the lock box code & key. Everything inside looked just like the pictures, and we weren't disappointed! If you're looking for some beautiful river views, right on the water, with your own private water access and dock, this is the place for you. We were in town for a wedding a few houses down, and this place couldn't have been any better for us. We were able to walk to & from, which was a huge bonus for after the reception...Cheers :) We enjoyed eating out a couple times in town, and really liked Brick Wood Fired Bistro & Traders Seafood Steak & Ale. We would highly recommend this property for anyone looking for a peaceful river stay, and will surely return someday in the future! Thanks for your hospitality!

What an amazing home! Bob was a great host. All of the rooms were very clean and there’s everything you will need at hand. Super comfortable beds. The views of the river are incredible with so many places to relax from the living areas to the outdoor deck on the second floor. The screened in porch was so comfortable. Fishing from the dock was a joy and just a great place to hang out and enjoy the water with our family. My son caught his first fish off the dock! The kitchen is a cook’s dream. Again, theres everything you need to prepare meals. Loved the huge kitchen island! Don’t forget to just stand and enjoy the view of the dock and river from the kitchen window. The downstairs den and bar area was just perfect for relaxing and watching tv. The house is on a cul de sac with only a few homes…very peaceful. We loved this place and plan on coming back again for our next trip! Thank you Bob for sharing your little slice of heaven with us!

Lovely stay on the water! Mini beach is an added bonus. Great restaurants nearby!

Beautiful place to stay. Quite peaceful area with friendly neighbors. Home was cozy and welcoming. Kitchen had everything you could need. Amenities were amazing. Had a spectacular time would definitely come back to stay again.

The house was wonderful -- clean, simply furnished, a more-than-adequate kitchen and bathroom. Beds extremely comfortable. The pictures suggest the back yard is on the water....there is actually a house behind Janet's house. BUT, there is an easy-to-access dock that was just wonderful. The single negative? The bugs!! Not anything controllable by others, of course, but did discourage us from the walking of the island we hoped to do. The end of the dock was our refuge -- and the view was just wonderful. Birds plentiful. The people of Smith Island were welcoming, gracious, patient. No exceptions. I am grateful they offer such hospitality.

This house and these hosts represent the very best of Airbnb. I checked in on a beautiful Friday afternoon, but shortly after arrival, a storm hit the area that knocked out the power. Jenny and Dave were at the house to check on my welfare as soon as it was safe, despite a literal tree falling on their porch. I only live half an hour away, and could have easily gone home where there was still power, but decided to stay put where I was instead, and if that doesn’t tell you everything you need to know about how wonderful this house and location and hosts are, I don’t know what else to say. 10/10. I can’t wait to return for another staycation!

Beautiful place! My family loved it there. Perfect staycation. Lots to do just at the house! KJ was a great host.

Lovely place to disconnect from your day to day life.

Surrounded by trees and the sound of waves- perfect place to relax & unwind. Quick but steep hike to the secret beach. Cool spot and more shell than I expected. Kyli was a responsive host, answered all my questions. Also, recommended Island Hideaway for dinner and it was amazing. Homemade pasta and desserts made in house daily. Great views and delicious foods & drinks.

Our stay in Tall Timbers was fabulous, much of it thanks to the care, detailed information, and lovely accommodations provided by our host, Robert. He communicated extremely well through the whole process from booking to check out. Nothing was a mystery and everything was as described or better. The house is charming and in a lovely wooded location. it's isolated but close to many amenities and short drive to historical attractions, local businesses, and the beautiful Maryland coast. We had a particularly wonderful visit to the Tall Timbers Oyster Ranch which is walking distance from the house. We highly recommend this location and send our thanks once again to Robert for his outstanding hospitality!

Great place for a getaway! St. Michael’s is a wonderful town and so easy to get to from this lovely place! Was perfect location for our family ladies trip- plenty of space and just a quick trip down town to the shops and restaurants! - I think we’ll be back!

Pizza Friday was an amazing find! We spent a family reunion on the porch making pizza's in the oven. We obtained crusts from an Italian restaurant in California on our way and it proved to the perfect choice for us. We also enjoyed the dock and even caught a few crabs to show the kids. In addition we sat around the fire pit in the evenings. The beds were comfortable and everything was clean inside although we spent most of our time outside on the porch.

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 Airbnb truly felt like staying in someone's home. There were lots of items provided in the house -- from toys in the cabinets, to records to listen to and the kitchen was very well stocked with pans, plates and seasonings. Outside we loved using the crab pots (though we came up empty and didnt catch any crabs) and lighting a fire at the fire pit at night.

Elizabeth's house was perfect for our weekend stay in St. Michael's. The house sits right on the water about a 5 minute drive from the center of town. It was the perfect home base for the Ironman event we were attending in Cambridge. Elizabeth was incredibly responsive and provided thoughtful recommendations for our stay. If we are in the area again we will certainly stay again.

We stayed at Julie’s home with a group of friends and our families and had a wonderful time. The lakefront setting was incredibly relaxing—we found ourselves rarely leaving the property because it had everything we needed. From soaking in the hot tub to enjoying the game room, there was something for everyone. The kids loved having space to run around in the basement, while the adults enjoyed peaceful mornings and evenings on the screened-in porch. Julie was very responsive and answered all of our questions quickly, which made the entire experience seamless. We would absolutely stay here again!

We absolutely loved this place. It was a short drive to the bay and certainly worth it. The cottage was secluded enough from the neighbors and we could hear the waves with the windows open. The beach was a very short walk from the cottage and was also very private. We spent a good chunk of our time finding sharks teeth and relaxing on the porch. Grocery stores and gas stations are also fairly close. We even booked our stay for next year already.

We enjoyed our stay . Plenty to due . Easy to find . Closer to stores . Quite great country lake feel.