Search Vacation Homes in Chestertown

"This home was perfect for our 3 night stay. We came to spend time with our daughter who had moved to the area. The owners thought of everything and the little touches are what made this the perfect rental for our stay. Only downside was the weather did not allow us to enjoy the amazing views and cozy porches during our stay. Next time we visit with a group we will definitely stay here again!"

"Lovely home; welcoming and comfortable, very helpful and communicative property manager."

"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!"

"Very friendly and helpful host and a great property. "

"Great place, great location!"

"The home was cute, clean and conveniently located in downtown Annapolis! Owner was easy to communicate with & stocked with everything you’d need. Would love to stay here again!"

"Perfect place to stay for a visit to USNA or Annapolis generally. Property is beautiful and well stocked, and it made for an easy stay "

"The location of this property is absolutely perfect if you want to be near all the downtown action. Cute street and quiet inside . "

"We had a wonderful stay in this fabulous property. The location near gate 3 of USNA and the quick walk to downtown made it a perfect spot. The house was impeccably clean, comfortable and roomy. Cathy was exceptionally helpful throughout our booking process and stay. You will absolutely enjoy your stay!"

"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "

"Great and comfortable stay! Beautiful historic house and property Owners were so friendly and helpful"

"Loved the location and the pristine condition of the house. "