Kid-friendly holiday rentals in Kent County

We loved our stay at Cheryl’s place. She was very accommodating and communicative, and the home was very spacious, clean, and perfect for our needs. We would stay again!

This was a lovely place to stay on the eastern shore of Maryland. The house was clean and a perfect place to stay the night before our triathlon.

The home was lovely, right on the river, and felt....homey. It was the kind of place I would have if I had a home on the river. There were friendly neighbors who gave us some advice on what to do/not to do in the area and we had a lovely time. This might just be an annual trip for me and my extended family.

This was our second time at Leone's beautiful spot on the Chester River and it did not disappoint! It's such a beautiful place and beautiful location -- we absolutely love it!! Thank you Leone!!!

Beautiful location and the bikes, kayaks and fire pit all added fun and relaxation to our stay! Close enough to Chestertown to enjoy the farmers’ market and shopping and far enough out to be a peaceful retreat.

We had an amazing weekend and Gregory’s home was perfect. So clean and well equipped. Gregory thought of everything!! Highly recommend ⭐️⭐️⭐️⭐️⭐️

Tim’s house was perfect for our group of 4 adults and 4 kids. It’s very cute, clean, and spacious. His level of hospitality did not go unnoticed, he seemed to of thought of everything. The kitchen was well equipped for cooking if you choose to do that. We would definitely stay here again!

House was beautiful, clean and host was phenomenal. Highly recommend!

It was an extremely lovely apartment overlooking the beautiful Chester River! The apt was spotless, warm, inviting & had lots of amenities. Walter was beyond helpful: he rescued me when my rental car broke down out of town on the highway in the rain. You can’t ask for more than that!! Thank you for a wonderful stay!!

This place was really great! It looked like the pictures and was exactly as described. Where it excelled was going past that. The small details that we didn't expect. Kim really thought of everything and it felt like going to a friend's house that really pulled out all the stops. She set bikes out for us to use. There were beach chairs, a cooler backpack, picnic blanket all available for us to use. There was a snack basket for us. A gallon of water and water bottles in the fridge. The kitchen was fully stocked with anything we could ever need. The bathroom had extra toothbrushes and other things we may have forgotten. The area was very nice and the sunsets at the beach were beautiful!! If you read this far, stop, just book it already!

Our third stay, always perfect from location to cleanliness to responsiveness. We’ll keep coming back as we visit friends and family in Rock Hall!

When they say Restful ... they meant it. It was so peaceful and a very nice neighborhood. We stayed for 4 nights and were able to go to all the beautiful towns and natural beauty around. Close to St. Michaels, Easton, Cambridge. Wonderful hosts. With out own deck next to a lovely water feature. The bed was king size and perfect! I would recommend this to anyone. We will be back. Thank you Tina and Tony! Bette and Lou

We really enjoyed the space and the place. There is a clear view down to the water, and we sat on the dock listening to the fish break in the surrounding water, and had a Great Blue Heron fly right by us. We chatted with Kate and Charlie, who obviously love their place, and are happy to share it with others. The appointments in the apartment are beautiful, and it is definitely upscale! We plan on a return trip. Thanks for the stay!

Stephen's carriage house was a perfect fit for our weekend getaway in Chestertown. It is a lovely, roomy space for a couple. The living room was easy to relax in, and the bed was quite comfortable. The skylights offer nice natural lighting during the day, and the bedroom was naturally dark - good for restful sleep. All of the provided amenities made the stay convenient, including the wifi, tv, kitchenware and appliances, and shower. We chose this space due to its walkability and its proximity to our favorite restaurant, Modern Stone Age Kitchen, just a couple blocks away. FYI - this space is in the courtyard of a restaurant, so outdoor diners may be heard during the day and evening, but by the time we went to bed the restaurant was closing so it did not affect our sleep. Also, be aware that parking on N Queen St is Residential Only, so be sure to check for signs and park accordingly on nearby streets.

What a lovely place to stay, in a lovely town, taken care of by a lovely landlord. Appreciate everything-will return!

What a gem! This beautifully renovated home, located in the heart of Chestertown, exceeded all our expectations. It was hands down the cleanest Airbnb I’ve ever stayed in—so spotless, I wondered if we were the first guests. The location couldn’t be better: right on the main street, walking distance to restaurants, shops, and with the farmers market just outside the front door. Evergrain Bread Company, a fantastic bakery, was right across the street. The home is adorable and the layout was perfect for my mother, who has mobility challenges. The beds were also incredibly comfortable. Katie was a wonderful host and left us thoughtful touches—wine, an amazing cheese tray, sodas, and snacks. I loved starting my mornings on the front porch with a cup of coffee. This was a last-minute getaway with my mom, and we loved it so much we’re already dreaming of our next visit. Highly recommend!

Wonderful stay in Chestertown! Hosts go out of their way to may the experience pleasurable. Would 100% stay here again!

What a perfect weekend get away. The place was perfect. Extremely comfortable beds, lots of pillows and two deck areas outside. We cooked outside 2 nights - and loved seeing the bay from the deck. We used the nearby tennis and basketball courts, and spent the days visiting wineries and neighboring towns, and driving through the countryside. Groceries and restaurants require some planning and some driving. Loved our stay!

My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!

Great host who was responsive. Wonderful space with well appointed kitchen. Will be back.