Kid-friendly vacation rentals in Queen Anne's County

We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.

Ashli’s place was a great location for exploring Chestertown. It was an easy walk to downtown and the water. She was very responsive to all questions we had and very welcoming. The house was spotless and the beds were extremely comfortable!

Cannot say enough about the view - beautiful sunrises and sunsets. We all enjoyed our stay and found it very relaxing. It is convenient to town which made it easy to purchase our groceries and other sundries. All in all a nice spot to hold our annual family gathering.

One of the best Airbnb's I've stayed in. Lots of nice touches like the disposable toothbrushes and toothpaste if you forgot yours, all shampoo and soap provided, white noise machines in every bedroom, blackout curtains for all bedrooms, lots of cooking supplies. The kids loved the playroom in the basement and the provided crib was really nice as well. The location was really peaceful with ocean views and a nice breeze. Would highly recommend and would stay here again!

beautiful spacious home. great for my family of 6 to meet up with our USNA midshipmen. loved the back yard and living rooms

This was a perfect home for a 60th celebration. The home was spotless, beds so comfortable, kitchen well appointed. Host left touches for guests to feel comfortable and welcomed. Quiet neighborhood, great backyard and close enough to walk to stores, resturants and Washington College. I would highly recommend this home for a familiy or friends get away.

This house really is a beauty. Our family had a great stay here. The kids loved the double bunk bedroom and playroom. And Ryan really does a great job of being responsive and providing all the toiletries and supplies you may need while traveling (but may have forgotten to bring). We loved it and would absolutely stay here again.

We had a fabulous stay last weekend while we were in Chestertown for a wedding. Ryla was a fantastic host, providing ample information prior to check in, as well as accommodating our last-minute request for a later check out. The house was impeccable, with ample room for our family, a well-stocked kitchen with everything we needed to cook a great Easter breakfast, and beautiful furnishings and decor that still felt homey and comfortable. I would 100% stay here again and would recommend you book it quick if you are looking for an amazing house to rent in Chestertown!

Comfortable beds, spacious layout, great shower and great scenery

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.

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!

What a wonderful place for a peaceful, lakeside getaway. Upon entering the space i immediately wanted to move in! So cozy and spacious with great natural light. I loved watching the sun set beyond the lake. Kevin was a gracious and responsive host. I felt very welcome and cared for. Highly recommend!

What a great place to stay! Everything I needed, beautifully and thoughtfully set up, a block from downtown, and an pleasant walk (or drive) to the Chester River right through the historical section of town, especially in the morning or early evening when everything is peaceful. Many thoughtful touches upon arrival - right down to biscuits for the dog - and helpful things like a basket of travel sized toiletries in case I'd left something behind. The hosts were easily available if needed but explanations were clear and everything intuitively set up, so I didn't need a thing. Thanks, Beth and Bob!

We had the best stay. Couldn’t recommend more.

We found this beautiful place when we needed a dog-friendy rental for our large dog while visiting our son at college. The rental is in a fanatic location, a very short walk to the waterfront and downtown Chestertown and its great shops and restaurants. The rental was immaculate and very comfortable. It had everything we needed. The backyard was more private than we thought and our dog enjoyed playing fetch in the back. The bedding was comfortable and relaxing. The host was very responsive and helpful. Great experience! Thank you!

We needed a quiet and private space to relax. Jordan’s space was all of this. We stayed here for a month and hardly ever heard Jordan and her family. Jordan was quick to respond if we had any questions. The bed was very comfortable and the views of the water were nice.