The Oaks Waterfront Hotel

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The Oaks Waterfront Hotel sits on a secluded 10‑acre cove off the Chesapeake, offering a renovated boutique retreat minutes from St. Michaels and Easton. Stylish rooms, waterfront cottages and a two‑room Waterfront Suite feature king beds, soaking tubs, private decks, heated-bath floors and Apple TV. Mornings begin with a hot gourmet breakfast; on-site highlights include The Oak Room bar, seasonal outdoor pool, rooftop terrace, private dock and complimentary kayaks, paddleboards and bikes. Ideal for weddings and corporate retreats, the property combines historic charm, attentive service and easy access to Eastern Shore dining and waterways.