Search Vacation Homes in Chestertown

"Charming Annapolis house with a great location downtown. Very spacious and clean. Will definitely be staying here again! "

"As advertised. Great views, dock and decks. Inside is modern, functional and very clean. No complaints whatsoever."

"This place is amazing! Super clean, decorated exquisitely. Check in and out was a breeze! The outdoor space is incredible with water views and plenty of room. And let me tell you, this location is where you want to be- walking distance to entertainment and restaurants! The host communication was on point, I would definitely stay there again!"

"Clean, Spacious, and exactly as advertised! "

"Can’t wait to come back during warmer weather. It was a perfect over night stay. "

"Our stay was incredible! The house is beautiful, it is super spacious with tons of perfect places to congregate and hang out. The rooms were all extremely comfortable and the beds had high quality mattresses that made sleeping so enjoyable. The views and sunsets were spectacular and our group loved spending our evenings enjoying the hot tub. The house’s location is perfect as it is not only right on the water but it’s just under one mile from the (albeit super tiny) town of Rock Hall. I’d love...

"We were in town for some fun on the water and a visit to the Naval Academy. We were able to park the car for the weekend and walk everything, great location. The house is very nice, a lot of space for the 4 of us. We look forward to visiting again for football season!"

"6 women for the 6 bedroom home. The house was great for our weekend. The only complaint was that the weather did not allow for more outdoor activities, though we had plenty of space inside to enjoy ourselves. The house has all the amenities and more. "

"We felt so comfortable and relaxed in this home away from home - it was beautiful and the location was perfect - so close to downtown - we were able to walk everywhere! "

"a great place to unwind. "

"6 adults for a wedding Check in easy, very comfortable home with lots of space. Owners are great people to rent from. They helped us connect with a neighbor whom delivered fresh steamed crabs ready to eat. Kitchen is very well equipped. Also very close to bike trail. The last Saturday of the month the local firemen put on a chicken/pulled pork BBQ. Food was excellent. "