A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Over 4,500 square foot home with five bedrooms (Plus two sleeping lofts for kids), three baths, expansive screened-in porch and massive deck overlooking a wide tributary of the Chester river on the Eastern Shore of Maryland. This unique family-owned ...

This private waterfront river home in beautiful historic Chestertown has its own private pier and pool - all on a quiet cul de sac. Enjoy the view from the river porch of the Eastern Shore sunset over glassy water, pick some Maryland Blue Crabs caugh...

Breathe in the fresh waterfront air and enjoy a laid-back stay on the eastern shore of Maryland when you book this expansive home in Chestertown! Highlighted by 5 bedrooms, 3 bathrooms, and a wraparound porch, this vacation rental offers a comfortabl...

Welcome to the waterfront Twin Ponds Lodge, built in 1987 and for many of its years was used as overnight accommodations for hunters. Many guests have felt they were staying in a rustic cabin in one of the Country’s National Parks. If you are a wildl...

This exceptional 5-bedroom, 3-bathroom shore house sits on a 1+ acre waterfront lot and boasts endless nautical activities, including kayaking, a private pier, and a large pool overlooking the Chesapeake Bay. Offering a welcoming interior and providi...

Enjoy a beautiful spacious 5 bedroom 3.5 bath home in a quiet wooded setting overlooking the Magothy River. The home includes two master suites: one on the main floor and one on the second floor. The second floor master suite has a jacuzzi tub and op...