Search Cottages in Chestertown

"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"

"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"

"Easy and flexible check in, clean and comfortable in a great location. Darling home. "

"It's a beautiful location and we enjoyed our visit."

"Had a lovely peaceful stay. Great amenities."

"We live in Washington DC and wanted to get out of town for inauguration weekend, so we stayed at this home. This was our second time staying here and we will definitely be going back. The home is perfect. Super cozy, super clean, and very quiet. The hosts are the nicest people ever, which makes staying there even more pleasurable. "

"Perfect little cottage for 4 adults and an infant. Loved its location! "

"10 family members from age 88 to 10 years old. It’s our 2nd visit and we’ve not been to any place more welcoming and peaceful. The location is just heaven and the docks and water views are just unbelievably gorgeous. It’s going to be an annual trip for our family."

"Very quiet street, our stay was relaxing and just what we needed! "

"Lovely home with everything you need."

"Absolutely amazing place for my husband and I to relax with our midshipmen. Very clean, beautifully decorated and the view on the dock each morning was stunning! Close to restaurants (loved 3 B’s Bakery) and host was awesome! "