Family-friendly vacation rentals in Chestertown

Sue’s place had great views and that cozy cabin feel. She was a great host and was very willing to accommodate us. The Airbnb was exactly as it was described. The surrounding town was also beautiful and had excellent places to eat. Well worth the stay.

In town for the Military Bowl and location was perfect. Loved the yard and would love to visit in the warmer months! Yarrow was excellent and had great recommendations! Highly recommend!

A beautiful home with gorgeous views of the bay. The host was super responsive and helpful.

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.

Staying here made our family wedding stay away from home, a very memorable and fun weekend for the whole family. Muvh better than being stuck in a hotel with lots of kids!!

Brandon’s place was great. It was perfect for our anniversary getaway. The hot tub was clean. The house was clean. We very much enjoyed our time at this place and in the city.

beautiful location on the water, well-stocked home. very enjoyable for a family weekend!

Absolutely beautiful. It brought so much peace. I loved it. My wife and I enjoyed our stay for our honeymoon. We want to try and make it a yearly visit because it was that good. It was hard to find the place when it was night because it’s pitch black but other than that, a flawless stay.

The cottage was adorable and extremely well equipped with kitchen utensils and bath products. We didn't end up bringing our pup and regret it because the outdoor space is HUGE! The location was better than expected as it's an easy walk to the water. 5/5!

Ingrid and Jay were very welcoming - they made us feel like family friends instead of Airbnb guests. The carriage home was charming and decorated nicely. It felt like home for the weekend!

Our most favorite Airbnb! Beautiful, peaceful, and close to charming Chestertown. PJ is such an accommodating and gracious host. Cannot wait to come back soon. 💙

Rafi was a very friendly and helpful host. We had a great time in this quiet neighborhood.

Nice quiet neighborhood, host was very flexible and accommodating

Absolutely beautiful home and neighborhood. Mark made it easy and clear every step of the way. We had a wonderful, comfortable stay.

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.

Had a nice stay while in the area to visit my nephew at the Naval Academy. The basement apartment is very comfortable. Area is nice and quiet and my dog loved having a yard to run in.

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.

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.

Marissa’s home was beautiful and had everything we needed - plus some. Plenty of clean/comfort space and restrooms for our party of 6. We had such a relaxing, warm stay during a snowy January weekend - even smores! Marissa was always responsive and provided suggestions for shopping and dining in St. Michael’s. It was lovely all the way around! Highly recommend this home and working with these owners. Top notch!

Kimberly’s place was a home away from home.. walkable, peaceful, clean environment just like we wanted! We had no issues finding parking right outside the place everyday . Everything we needed was there. She was very responsive. All about Kimberly’s place was just perfect! We had a flawless one month .. surely coming back Kimberly!!

This lovely house sits on a private lot with spectacular water views. The pool is pristine and was a perfect depth for both the children and the adults. in our group. There were 10 of us (three generations) and we had plenty of room to feel comfortable.

This was one of the best spots we’ve stayed at! We were in Baltimore to film a music video and it was so home to come back to after filming and just relax! Shower was amazing and beds were super comfortable!

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

Amazing property, unique home, peaceful views. This is an overall great place to stay; I would love to come back if we are in the area again!