Family-friendly holiday rentals in Chestertown

This house was absolutely central to all the activities we planned for our trip to Annapolis. Located in a wonderful neighborhood and a beautiful walk away from a tasty coffee shop!

We had an excellent stay! We were able to get a parking spot right out front before the post-work rush. The park across the street and neighborhood were very nice. It was a 20m walk to Fell’s Point and the grocery store and waterfront were a 10m walk. Brandon was a communicative and very thoughtful host. We would certainly stay here again!

Fantastic stay. Veronica was an excellent communicator from pre-booking to check-out. House was very nice, but the pool was exceptional. Home was as described. Thanks for a great weekend.

This home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!

We had a wonderful stay at Brenda’s place! The pool is amazing and the whole outdoor area is great. With the grill, chairs and tables, outdoor fire (two of them!) we had such a great weekend escape. Very quiet area, we didn’t see the hosts the whole time which made it feel private. They were so responsive and helpful all weekend. Wonderful stay and we will definitely be back!

Brandon's place was absolutely perfect! We couldn't have asked for a cleaner or more comfortable space. The location was great and Brandon is an amazing host. We would definitely stay here again!

We thoroughly enjoyed our stay at Laurie's home! It was a great location and the home matched the description. We had everything we could have asked for and more, and Laurie was a great host. Would definitely stay there again!

Great place to stay with family and friends. Very quiet area and a lot of parking available. Instructions was easy to follow in and out. We recommend this place for others.

Perfect location if you’re in Annapolis for a game or just to visit the city. Christopher’s house was the perfect location and distance from everything in the city. Also, very spacious and nice house perfect for me and my 4 other friends.

We can’t say enough good things about Megan’s place. Our favorite part was how well-appointed the kitchen is, but it’s all great. Very walkable/bikeable city, so you can leave your car behind.

Stanley's place was a great for our two night stay. It is secluded and very private - the garden offers a private oasis and there's plenty of parking! We had four guests stay with tons of suitcases and space was not an issue. The house is older, but very clean. There are three bedrooms that can sleep 2 adults each. The bedroom off the living room is a little warmer than the rest of the house, just an fyi. The kitchen is well stocked with utensils, plates etc. Overall a great stay!

We had the most wonderful stay at this Airbnb! The home was absolutely perfect! Clean, cozy, and stocked with everything we could possibly need. Liz went above and beyond to make our trip special, even decorating for my boyfriend’s birthday and leaving us some sweet treats. It was such a thoughtful touch that really made us feel welcome. The fenced in backyard was a dream for our dog, and we loved how peaceful and private it felt. One of our favorite parts was how easy it was to walk downtown, just a short stroll to all the shops, restaurants, and waterfront. Truly a perfect weekend getaway spot. We would 100% stay here again!

I had a fantastic stay at this Airbnb! The location was perfect—super convenient, just a short walk to downtown and the convention center, making it ideal for both leisure and business. The place was spotless, thoughtfully designed, and well-stocked with everything I needed, from kitchen essentials to fresh towels. The keyless entry with the door code was a breeze, making check-in and out seamless. The host was incredibly proactive, communicative, and quick to respond to any questions, ensuring a smooth and stress-free experience. I’d highly recommend this listing to anyone visiting the area—can’t wait to book again!

My wife and I came to Baltimore for a few days to get away and see the sights. The house become an important part of our getaway. First, it was in a very charming neighborhood. Right next to a very nice park. More about this park later. At night the entire tree-lined street lights up making it look magical. The home itself has a certain charm and we felt at home the moment we stepped inside. The house is a short drive away from the Inner Harbor, which was the main attraction of our trip. But we found plenty of other places to visit during our stay. Our final night, back to the park for a leisurely walk to the other side where we found an ice cream shop! What a wonderful way to finish up our trip sitting on a park bench, eating our ice cream, watching the people walk by. Rafi, our host, was fantastic. He responded to all of our questions very quickly and was very friendly. Rafi was the perfect host. Overall we completely enjoyed our stay here. Thank you so much Rafi!

Wonderful host—I felt right at home. Had conversation prior to arrival and felt like I knew her very well before arriving. The view was spectacular I could have just sat on the patio and watched the woods and water all day. Was there for a school reunion so I had other activities that I had scheduled. This was by far, the best Air B&B experience I have had. Fantastic host, comfortable, and stunning scenery. I am going to try and revisit soon.

We booked Mark's house for extended family over a graduation weekend. It was comfortable and charming, kitchen perfectly stocked and bathrooms pristine. Relaxing for a weekend visit, with a lovely walkable neighborhood. Would absolutely book again!

Words can’t describe how incredible this home/property is! You have the option to just sit by the water or in the hammock watching the birds play and fish jump, or you can do one of the MANY activities Molly has provided for you. Kayaks, canoes, paddle boards, pickleball, yards games, pool activities, etc are all provided. The family room is all windows so it not only provides the most incredible breeze- it is great for enjoying all the sights even if you’re not outside in it. Inside there are tons of toys for kids- you do not have to bring a thing if you have kids. They have inside toys, outside toys, kids life jackets, goggles, water balloons, rafts, floaties, pack and play…. Molly and her family have thought of it ALL. We are already talking about coming back. Molly was the best host- responsive, helpful and inviting.

We had an amazing time aboard the Zep Tepi! The boat is beautiful and spacious and the marina and setting are lovely! If you want to really get away and experience sleeping with the peaceful rocking of a boat, book this now! Chelsea was responsive and helpful as we got used to the workings of a boat too.

Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.

We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.

Dorie and her daughter are wonderful hosts. The area is nice and walkable. We took a walk everday while there. Central to shopping and parks. It is a family neighborhood. Dorie initiated contact several times during our trip to see if we needed anything, to clarify check out instructions, and to let us know she was available if needed. This apartment is upstairs, the host lives below. You will enter through your own private entrance. As far as the dust or noise others mentioned...that was not our experience. This isn't a hotel. Theres no housekeeping. The homes aren't brand new. Its a charming apartment with great hosts in a sweet little neighborhood. Think of staying at your aunts place, not the Ritz. If your standards are perfection, you'd likely prefer a hotel. If you are more relaxed and want a ready made apartment that feels more like home than a vacation spot, this is your spot. I found the apartment clean and comfy! Age is not dirt or grime. Just a normal spot! Airbnbs are homes

We’ve stayed here for a few years now. His place is always clean and quiet. Beautiful location and very comfortable.

We were in the area for a lacrosse tournament and hotel living can get old. The Farmhouse was a great break from that and exactly what we were looking for. All the amenities were greatly appreciated.