Private Peaceful Waterfront House with Pool & Hot Tub

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...

Accommodations: Manor House - Five Bedrooms (including one Private Suite), three and one-half Baths, Sitting Room, Den, Formal Dining Room, Kitchen and Sun Room (Sleeps 15).In 1659, a Mariner by the name of Peter Bovery was granted acreage for wh...

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...

Rock Hall, know as the "Pearl of the Chesapeake" is located directly on the Chesapeake Bay, Bay Breeze Inn is located right on Main St, right in town. A grand home circa 1884 that offers large indoor and outdoor entertaining spaces, perfect for large...

Cool waterfront contemporary with retro vibeLocated on the serene banks of Skipton & Mill Creeks, this home offers plenty of comforts disguised as contemporary cool. The open living area, situated on the second floor, includes a beautifully renov...