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.

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!

Natalie’s place was just like the pictures. Everything was clean and well stocked for our stay of 6 adults. The sunsets were beautiful from the dock and the kayaks were a definite bonus! We enjoyed time outside on the dock, deck, and in the hot tub! The beds were very comfortable and our stay was great!

The ultimate Maryland water experience. Beautiful house with perfect amenities to enjoy the bay. With the dock, the view, the crabbing, the fishing, and the kayaking, you save time and money by having everything at your fingertips. The hot tub was wonderful even in summer. The house has everything you could want for a relaxing stay. We ate the crabs we caught every night for a week! Plenty to do and see in the area, too. Definitely want to return!

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!

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.

This 5th Wheel is like a water front Tiny Home. It is accurately described and pictured in the listing. It was clean and had everything needed for a short stay. It is in a working boat yard so it was cool seeing the owners working on and moving boats around. Also had some nice conversations with some of the people who dock their boats here. The marina itself seems very healthy. Clear water loaded with schools of bait fish so the blue heron, great egret and osprey were easy to spot. Unique and fun Airbnb. Highly recommend.

Stayed here Memorial Day Weekend with my family of 4 and dog and had the most lovely time! The house is very clean and conveniently located to everything! Thomas was an excellent and communicative host. We will most certainly stay here again!

This cottage was a gorgeous place to relax with my wife for her birthday. The proximity to the bay cannot be beat - especially since she made kayaks available for our stay. I would happily re-book next time I am in the area.

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!

The cottage was in a perfect location for my sisters and I to stay for our "sisters weekend" escape. The setting is beautiful and so relaxing. There was plenty of room for us and everything was clean and tidy. We took advantage of the kayaks during the day and had a wonderful fire with s'mores in the evening looking out over the water. We will be back!

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!

Perfect house for our needs! Great, central location with many restaurants within a short walk or drive. In a beautiful residential neighborhood. House is well-maintained & -appointed. Mark was super friendly and responsive leading up to and throughout our stay. Highly recommend - thanks!

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.

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

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 was fantastic. The space was really wonderful, quiet, and a great place to recharge.

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.

The Pilot House on the Inn at Haven Harbour property was fantastic! For a family with kids this is the perfect amount of space to be able to spread out with two living spaces and 3 bedrooms. We loved having the outdoor dining space as well. The beds were all comfortable and having the kitchen fully equipped was a huge bonus. The location was probably our favorite aspect- just 2 minutes walking to the pool, the on site restaurant, the playground/beach area, etc. and just a 4 minute drive (15 minute walk) to the Rock Hall Main Street. Overall a great experience and stay!

Piney Grove is perfect! We had our extended family for the weekend and hosted a graduation party for about 40 people. The farm is the perfect location and venue. The beds are amazingly comfortable and all on the second floor. The main level is a livable museum! The kitchen is huge and VERY well appointed. The dining room is an exceptional place to host a dozen or more, and the parlors are perfect conversation areas. But the porches front and back? Those may be the best part of this place. We had our party in the back and it could not have been better! Wait—the actual best part of this place was Jennifer, who made sure we had everything we could ever need and was the most amazing host! I wish we had discovered Piney Grove Farm years ago—it’s our new favorite!! I wish I could give this six stars!