Chestertown Vacation Rentals

"Where do I even start with how GREAT this rental was. Everything from start to finish was exceptional. When we arrived, getting into the house was no issue at all. It was exactly per the instructions we received for check in. We walked into the IMMACULATELY clean house and couldn't believe it. I mean, not a spot of dirt to be seen. We arrived later in the evening so explored the house and then went to bed in extremely comfortable beds. So comfortable that we looked at the mattress type to...

"Property is well maintained and very clean. Great location for airport, DC and Annapolis. Only suggestion is to add a coffee pot. One cup at a time was a little annoying at breakfast."

"Family gathered for the weekend to celebrate our parents/grandparents who both recently passed this year. They owned a house in Rock Hall for 25 years, where we had regular family gatherings, giving us so many fond memories. The weekend was bittersweet as we returned to Rock Hall for the first time in years. The house was lovely, cozy, has a great deck, fire pit and shed with well taken care of bikes and games. It was clean and beds were comfortable. We would stay there again. Thank you for...

"The property is very well maintained, pleasant welcoming atmosphere. One would hardly tell if neighbors existed due to the peaceful environment. Anybody wishing to stay here should not think twice, JUST GO FOR IT"

"We stayed at this beautiful property for my 50th birthday Girls trip. We were 15 of us. The house is very spacious, attractive pool and water facing sun room. Some of the rooms have gorgeous views of the water. They have a pickleball court, large family room where we could all hang out together"

"While the cottage may have some of the historic/ older quirks, it is a wonderful (and beautiful ) property that we would highly recommend! We loved the walk-ability to downtown Annapolis and the Naval Academy. Despite its close location, it’s quiet at night lending to a good nights sleep 😊. The owner provided us some great insight on the location as well. "

"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"

"We very much enjoyed our stay, relishing the peace and quiet of the property as an offset to our busy wedding week. The house was spacious and well outfitted, and we all enjoyed downtime in the pool. Glen was very helpful at answering all of our questions. We left the galley stairs to the young adults traveling with us. :)"

"Debbie was a great communicator and very generous with allowing us to check in early - such a treat! The kitchen is well appointed and we were all impressed with the great bath towels and bed linens. The one thing to point out is that while this is a water front property, I didn't realize from the pictures, that its on a cliff, so you couldn't fish from the front of the property like I was imagining prior to arriving; luckily the walk to the beach was a short one so our kiddos fished from...

"Five star"

""Oh, down in Chesapeake Catching rock around fishing creek The soft-shell crabs play hide and seek Down in Chesapeake." We LOVE the Chesapeake area and have stayed up and down the bay, mostly midway and lower. This area on the upper bay is so close to Philadelphia and, although there are tourists around like us, it doesn't feel touristy unless you go into North East, downtown (which is still worth eating a meal or getting ice cream in that cute little town)! Our stay felt private, and we had...