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The Oaks Waterfront is the most enchanting of Eastern Shore wedding venues. It’s a country inn tucked back along a winding road set against the backdrop of a quiet cove just off the Chesapeake Bay. The Oaks is a picture perfect setting for a Maryland waterfront wedding. Surrounded by 10 acres of scenic Maryland landscape and waterfront, The Oaks Waterfront sets the perfect ambience for your celebrated occasion.

SURROUND YOURSELF IN COMFORTABLE ELEGANCE

An easy trip from Washington DC and minutes from St. Michaels, Easton and Oxford, The Oaks offers spacious St. Michaels, MD accommodations, and stunning waterfront event facilities. We are close enough to make your getaway spontaneous, your conference productive, or your wedding a joyous gathering of family and friends. However, in every other sense, we’re far enough away to become your own private corner of the world. Locally owned and managed, The Oaks provides an exclusive retreat and venue with the feeling of home.

RELAX IN LUXURIOUS ROOMS, SUITES & COTTAGES

In our main building, you can choose from a variety of graciously appointed rooms with upgraded options like water views, private balconies and soaking tubs, or indulge with all three in our Waterfront Suite. If you’re seeking more space and seclusion, our cottages are the perfect choice. They all feature king beds, luxury baths with soaking tubs, and epic water views. Regardless of which option you choose, you’ll be able to enjoy our high-end amenities, as well as a freshly prepared hot breakfast each morning.

Nestled on a secluded cove on the Eastern Shore, our beautifully renovated waterfront event venue offers an unparalleled backdrop for one-of-a-kind weddings, productive meetings and joyous celebrations.

ENJOY A PICTURE PERFECT SETTING FOR RELAXATION

Tucked back along a winding road set against the backdrop of a quiet cove just off the Chesapeake Bay, The Oaks Waterfront Hotel is a picture perfect setting for a Maryland waterfront wedding or Eastern Shore getaway. Surrounded by 10 acres of scenic landscape and waterfront, our Maryland boutique hotel sets the perfect ambience for your celebrated occasion. Indulge yourself. Stay as long as you’d like. Your world will still be there when you get back.

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