Holiday rentals with a kayak in Dorchester County

This was a great house for our teammates to stay in for the weekend!

Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.

Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!

This was our second year staying here and the place is perfect for our family. The layout and the ADA features were exactly as how they described them to be. This allowed my mother in law to be able to go out on the pier and enjoy her morning coffee. My daughter and I enjoyed the kayaks one morning. It was very relaxing and peaceful.

This place is amazing. We loved it and will be coming back soon. Jo was amazing and very responsive. Jo answered all text with questions we had and made our trip amazing. I recommend anyone looking for a peaceful water front getaway choose this house you won’t regret it. Very amazing place and host.

My family of 10 had a great stay here! There was plenty of space to spread out and the location is perfect and serene. We were able to fish out on the dock and caught a few spot! One of the friendly neighbors even stopped by to offer some raspberries from their bush and extra firewood. We did run into an issue after check in with one of the bathrooms, but Karina was quick to respond and sent someone out to handle it as quickly as possible. Thank you for the wonderful stay!

We had a truly wonderful stay at this beautiful home! The place was spotless and very well maintained, and we felt comfortable from the moment we arrived. There were plenty of activities to enjoy as a family, and we created some unforgettable memories here. The host was incredibly friendly and responded quickly to any questions we had, which made everything even more enjoyable. The surroundings are absolutely stunning, and the sunset views were nothing short of magical. We would love to come back again!

This was our second trip to Bob’s and we plan to return! The crabbing was great! Beautiful views and loved the lighting at night. Great hot tub! We loved having enough space for all of us to hang out in multiple areas. Nice upstairs balcony. Loved the kitchen! The kids loved splashing and playing at the private sand beach. Screened in porch was a very comfortable place to hang out! Can’t say enough good about this place!

We recently stayed at this beautiful Airbnb tucked away on a secluded property in Oxford, and it was exactly the reset our family needed. The house was spotless, cozy, and surrounded by nature—offering the kind of quiet you don’t realize you’ve been craving until you hear it. What truly made this stay exceptional were the hosts. We arrived by boat at a nearby marina, and due to our boat’s deep draft, they picked us up to bring us to the house. That extra effort made all the difference, especially with a group that included kids and family coming in from different ends. The home felt like a retreat—private, peaceful, and welcoming. It gave us a much-needed chance to reconnect, recharge, and create some lasting memories. We’d absolutely stay again and recommend this home to anyone looking for an escape from the hustle without sacrificing comfort or kindness.

We had an amazing stay! Daniel was an incredible host—friendly, responsive, and made everything so easy. The property itself was absolutely beautiful, with a rustic charm that made it feel cozy and welcoming. The house was clean and had everything we needed for a comfortable stay. We truly enjoyed our time here and would absolutely stay again. Highly recommend!

The house is wonderful! We enjoyed being in the fenced backyard with our dogs, hanging out on the dock watching the boats go by, or just sitting in the house admiring the view through the huge picture windows. It was very clean and had all that we needed for a relaxing get away weekend. Natalie was very responsive and very helpful with great local suggestions. Emily's Produce is only a few minutes away and has everything we needed, including fully cooked meals. We can't wait to come back!

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!

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

This place was exactly what my partner and I needed to rest and relax and spend quality time. The private beach made us feel like we were on our own resort. The home itself has even more comfort and amenities than you see in the pictures. Beautiful furnishings, clean, full of light. The main bedroom is upstairs and is positioned towards the beach so you can enjoy the most beautiful sunrise without leaving your bed and hear the waves while you sleep. The balcony off the bedroom is another great seating area if you’re looking for quiet time. There is a super comfy couch in the living room which makes it a great place to relax and watch tv or play games. There are some games available at the house. bikes and kayaks. We spent a nice day lounging on the beach chairs and on the porch chairs before making dinner, didn’t need to bring kitchen supplies since most were available. Did bring own spices. Tim was great and all his tips and info pre arrival were super helpful. We’ll definitely return

Had a wonderful stay! The entire family enjoyed the little beach and dock. Our son caught us crabs to eat every day and our daughter was in the water constantly! Very peaceful sitting on the back deck.

Beautiful private hidden gem on the water, perfect place to escape for a weekend.

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!

Despite living in Virginia for the last 10 years, this was my first visit to southern coastal Maryland in decades. The beauty of the area is truly striking. Teresa’s rental was itself charming and located in a pretty area, but also only a short drive from other locations and activities worth visiting (e.g., St. Mary’s county). Teresa was responsive at all times, which included helping to remotely resolve a minor interruption in the internet service. Enjoyed our five days there and would have liked to stay longer.

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.

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

Great property & host. We booked our reservation because of the appeal of the backyard/property, but the home was just as nice. One of the cleanest properties we’ve ever been to. Clear and easy communication with the host - easy to check in and out. We hope to come back next year!