Eastern Shore Rentals

Enjoy the Land of Pleasant Living in these wonderful vacation rentals on the Eastern Shore of Maryland. All venues are available for short or long stays. The properties are ideal for a weekend get-away, family vacations, special events, artist-in-residences or yoga retreats. The properties are managed by Prince Raimond Ventures.  Contact us to learn more.


hebe fountainCharming Apartment in Chestertown

One-bedroom apartment located in historic Chestertown. Perfect for enjoying this historic, artistic town on Maryland’s Eastern Shore. Accommodates 2 guests. More >>


Sunview Cottage on Chesapeake Bay

Modern 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from wrap-around deck. Perfect destination for families and friends. Located in the scenic, serene environs of the Eastern Shore of Maryland in Tolchester, 12 miles from Chestertown. Accommodates 5 guests. More >>


Bayview on the Chesapeake Bay in TolchesterBayview by Chesapeake Bay in Tolchester

Quaint one-bedroom cottage. Ideal for a weekend getaway or longer stay to enjoy the culture, history and cuisine of Maryland’s Eastern Shore. Enjoy bird watching & sunsets on the Chesapeake Bay. Located in Tolchester, 12 miles from Chestertown and 5 miles from Rock Hall. Accommodates 4 guests.
More >>


Cozy Apartment in ChestertownCozy Apartment in Chestertown

One-bedroom apartment in historic Chestertown. Close to Washington College, Downtown Chestertown, Fountain Park and Heron Point. Accommodates 2 guests. More >>


Properties managed by Prince Raimond Ventures LLC