Enjoy the Land of Pleasant Living in these wonderful vacation rentals on the Eastern Shore of Maryland.  Available for short or long stays. The properties are also available for events such as weddings, anniversaries, Bay-to-Table Banquets and more.

Charming Apartment in Chestertown
Accommodates 2 Guests

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

A delightful one-bedroom apartment located in historic Chestertown. Close to Washington College & Heron Point.

Delightful Duplex in Chestertown
Accommodates 4 Guests

This wonderful 2 Bedroom/ 2 Bath Duplex is located near downtown Chestertown and Washington College. More >>

Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from wraparound deck. Perfect destination for families & friends for Bay & Sunsets. Located in the scenic, serene environs of the Eastern Shore of Maryland in Tolchester.  More >>

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 >>

Properties managed by Prince Raimond Ventures LLC