Family-friendly vacation rentals in Chestertown

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.

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!

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.

Super nice place. Probably the most well stocked place we’ve stayed at. Walkable to everything and still in a quiet location. Bathroom was spacious and clean! Hot tub in the courtyard was a nice touch. Parking was a little short to come by but we always found a spot on Baltimore St right next to Patterson Park. Charmed Coffee was a great place for coffee and breakfast…dog friendly! 10/10.

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.

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.

Great stay in Annapolis. The property is located at the end of a quiet, dead end tree-lined street. A short and pleasant walk to the heart of Annapolis with dining and shopping options along the way. The property was clean and appeared exactly as the shown in the photos.

Shawn's place is great! It is well-cared for and has everything you need to enjoy the indoors and the outdoors. The views of the water are beautiful and you can spend a lot of time watching the different birds. Getting there is easy and not far from restaurants and grocery stores. Shawn makes you feel special and wants to ensure you have a wonderful stay. Hope to go back soon.

We stayed at Richard's house for 3 nights in late Spring. Its an amazing place, with great views from the rooms. There were lots of great places to see nearby.

Everything was great! Would stay again.

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!

Great stay. Nicole was a great host. We were in town for our nephews graduation from the naval academy. Our family of four was comfortable. Very well supplied with lots of extras/special touches. Would definitely recommend and would stay again.

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!

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 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

Great place and location. If you want something quaint but still close to downtown this is your spot

The cottage was the perfect serene retreat. The kitchen was well stocked so that we did not need to go to a restaurant for many meals. We especially enjoyed sitting on the dock to read while taking in the gorgeous view. We also brought our own kayak and took advantage of the boat house where we could store the boat overnight. Ann was a fantastic and responsive host! We will be back!

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!