Family-friendly vacation rentals in Chestertown

Mr. Bill made accommodations when the Airbnb I had originally planned for fell through. He made the transition quick and even made sure my weekend was blocked off at the new Airbnb and not compromising our plans. Forever grateful for the last minute switch

Overall a great place. It's only a short 10-15 minute walk on sidewalks to the rest of Eastport and the Annapolis harbor area, but in a quiet neighborhood that isn't busy with vehicle or foot traffic so it was easy to enjoy the lovely garden and patio outside with minimal city noise. It is accurate as described and from the photos. Did not experience any problems in the neighborhood or feel unsafe.

This house is uncommonly beautiful. There is something in every space worthy of contemplation whether it is coffee table in the living room that has a turn of the century industrial feel to the lacquered kitchen countertop that has sealed in the natural beauty. I spent the weekend in awe of its intricacies. I was in town for a wedding with my family, but noted how the whole house including the outdoor space included everything a beachfront house would have to enjoy an extended summer vacation for the whole family. Outdoor space was well equipped for outdoor activities and entertainment with fire pits, grills, hot tub, a plugin cooler for outdoor use. I only wish we’d been better suited to enjoy every aspect of the amenities provided. My favorite thing about this place was the view of the Chesapeake in all of her glory on full display from the living room window. Delightful.

Doug”s house is exactly as described and his communication was impeccable. My family and I truly enjoyed celebrating my birthday at this property. The pool is huge and there are seven bedrooms to choose from. The master bedroom has a sauna inside the room which was an added bonus. The only thing I wish they had was an additional full bathroom for 7 bedrooms. There is one in master and one in the hallway. There is nothing negative I can say. Even the cleaner, April was the best. I would definitely rent again and actually look forward to renting again 😊

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

Great location with lots of locations walkable and nearby. Peaceful neighborhood and great place to stay. Brandon had lots of helpful recommendations for restaurants, bars, etc.

This was a beautiful waterfront home! This home was well equipped with everything you may need! The host was available if we needed anything! Would definitely recommend!

This place is awesome!!! Very quiet and nice neighborhood. This was the place that I chose for our 11 th wedding anniversary and could not ask for a better experience. The kitchen is what I loved the most . Many places to eat near by and the Chesapeake bay is right there.

Great stay in a cute duplex in Arts District. Very clean, updated apartment close to restaurants and shopping. Perfect spot for a weekend in Annapolis.

We were the first ones to use the Cottage following the kitchen remodel. The new open floor plan is very attractive with beautiful views of the creak and Chesapeake Bay throughout most of the house. My wife is a chef so we cook most of our meals and the new kitchen was quite workable for all dishes great and small. Shawn was attentive as needed and even furnished us with pictures of the culinary equipment there, so we knew exactly what to bring. The area is quaint and quiet but there are lots of quality restaurants nearby, and Annapolis is a only short drive away. The Cottage feels like the perfect place to stay and write the great American novel or compose a symphony.

Love the back porch with water views, very peaceful. The cottage was better in person than depicted on the photos, such a cute place! The bed linens were cozy on super cold nights. Deale is an adorable town.

Ingrid was there when we arrived and was so personable! She was thoughtful when it came to having things for my girls to play with! Although we weren’t at the Airbnb much because our family lived right down the street, the beds were comfortable and my daughters loved the toy box! Thank you for having us and we’ll be staying again the next time we visit 🙂

Great place for families. Quiet and safe street. Just across the road from a wonderful park. Quick drive to local attractions and dining like Fells Point and downtown. Rafi is an A+ host with clear communication and local recommendations. We loved our stay; thank you!

We loved staying at Mark’s beautiful home for our daughter’s graduation. It was a mile to campus, up the block from Miss Shirley’s and very close to great restaurants. We were welcomed with flowers and candy when we entered his beautifully and uniquely decorated home. We wish we could have swung on the porch all summer but were happy to have had the weekend. If you have a big group and/or love old homes Mark’s house is ideal!

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.

Nicole greeted me warmly when I arrived and helped me into the unit. She was available and responsive for any issues. The place is great. Everything I could possibly need was provided.. Close to everwhere in Annapolis. Lovely to look out and to enjoy the back yard. A perfect place to stay. Wish I could have stayed longer.

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.

Great place for a getaway! St. Michael’s is a wonderful town and so easy to get to from this lovely place! Was perfect location for our family ladies trip- plenty of space and just a quick trip down town to the shops and restaurants! - I think we’ll be back!

Beautiful house and property, great location, and the host was super responsive. Hope to return sometime soon.

It was a great place to stay. The days we went were quite rainy, and the house looked like a homestay nestled in the woods. The house was kept clean, cozy, and quiet, just what I needed after a long tiresome day. I enjoyed their book collections as well. Although, I couldn't make use of the local suggestions they had in the house, I'm sure it was well-curated. Overall, a fantastic stay in a safe place.

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.

We so enjoyed our stay at Dorie's place! Peaceful and quiet while still being a quick jaunt off the highway, it was well-located for our trip visiting friends in Baltimore. Our 3yo loved the swing set in the backyard and the apartment door is situated right over a beautiful flowering dogwood, just perfect for your morning coffee. We appreciated the great price for a holiday weekend. Thanks so much!

We had a wonderful stay! The house and area are gorgeous, and Bill and his wife were incredibly friendly and welcoming. The pool and grounds were gorgeous and the house was very large and comfortable. We would love to go back.

Rita was a great host and we very much enjoyed our stay. The location was perfect for families traveling with kids. Our kids loved the outdoor space and the water off the dock is pretty shallow so no real fears about falling in the water. It’s a quick drive to St. Michael’s for food and shopping. Overall, a great spot.