Kid-friendly holiday rentals in Kent County

This was the perfect location for us to stay for Thanksgiving! This home is easy to find and near some wonderful restaurants!

Curtis was a wonderful host -- super responsive when we had questions, made certain we arrived safely and securely, had the house spotless on arrival and really took care to make us as comfortable as possible. Sleeping was a dream -- new mattresses and the freshest linens. Rock Hall is lovely, quiet bayside town for a real getaway, and an easy drive to other spots on the Eastern Shore.

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.

My family came down for our cousins wedding and had a wonderful time. The house and guest house were perfect everything was clean and inviting upon our arrival.

Exactly as described in great location to walk to the little downtown area.

We thoroughly enjoyed our stay. The location was perfect. The Bay was across the street. There were many extra Amenities available to us on the grounds. The house was in a perfect location, very well maintained, fully equipped, very cozy, and within walking distance to everything. The neighborhood was quiet and peaceful. Megan was the perfect host. She was very welcoming, friendly, warm, and responsive. Everything went smoothly and was exactly how she said that it would be. There were no unexpected surprises. We can't wait to go back!

Great stay! We will be back again.

We had a great weekend staying at Tim’s place. Everything was very neat and clean, and there was plenty of space. I would highly recommend this Airbnb.

It exceeded my expectations based off of the pictures I had saw. Super easy check in and they even left a handwritten card and some snacks for us. Thanks Josiah for the welcoming touch!

We were charmed by the comfortable design of Kimberly’s place. Great a/c, fully functional kitchen, lots of extras (water, snacks, oil, seasonings, coffee, tea, creamers, etc). Spacious for the two of us, this is a small apartment, with kitchen, LR with table, bedroom and bathroom. Everything is like new. We initially had some problems with the WiFi, but Kimberly and her husband kept working on it until we found a solution. Excellent communication! Close bike ride to town, beach, restaurants in walking distance, beautiful spot.

We had a very positive experience. The apartment’s rooms were clean and comfortable, and it always seemed sunny and nice. Most furnishings felt relatively new and fresh, and they even had a baby gate for our toddler. The downtown area is very walkable from the apartment, and there is a nice cafe right across the street. We didn’t require much contact with the hosts, but they promptly responded to the few messages we sent. We’d definitely stay here again when we visit in the future.

Tony and Tina’s home was very comfortable and peaceful. They were very pro active in communicating and accommodating in checkin and check out. They made sure the light was on as we arrived late. Very comfy bed!! Very nice!

My family and I had the perfect weekend. The cafe was fabulous and the sweet store next door was delicious and super friendly. We loved the market across the street and the gift store the apartment had everything we needed and it was very comfortable and clean. would definitely book it again.

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.

This spot is a very utilitarian unit but perfect for my dog and me. Very easy to walk to town, the bed was very comfortable and it was great having access to the backyard.

We had a wonderful stay here and would surely stay again! It was a beautiful spot, easy to get to, and the area is very walkable to shops, restaurants, a park, and bars on the main street. We appreciateed all the amenities (coffee, appliances, games, etc), and the combination of new designs in this preserved historic house. For a college town it was quiet and peaceful at night. We found the locals to be very friendly in this sleepy little town. If we weren't staying for a youth baseball tournament, we would have definitely taken advantage of the float spa on site. All in all, we had a wonderful stay!

This apartment was perfect for our family get together. Although we had a short stay, every detail made us feel very welcome. Michelle was very helpful and promptly mer our needs.

A great sunset view from the balcony, such a nice quiet river/bay beach, peaceful community to walk around. Would stay in again! Would note there’s 1 flight of stairs up as it’s a 2nd floor condo of sorts; and a big hill/stairs down to the beach. However, also a parking lot if needed to drive to the beach. Beach chairs were nice to have. There was no cooking oil but I think we left some :) I would only ask they replace the dining room chair with the hole in the seat. The pool was closed and that was not expected! Adam was very responsive when we messaged.

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