#1The Oaks Waterfront Hotel
The Oaks Waterfront Hotel is a beautifully renovated 1902 colonial-revival waterfront hotel and exclusive wedding venue set on 10 secluded acres on Oak Creek off the Chesapeake Bay in Easton, Maryland (near St. Michaels). The property became a member of Historic Hotels of America in 2025 following a substantial 2022 renovation. Couples buy out the entire estate for a full weekend, with ceremonies on the manicured ceremony lawn surrounded by lush gardens or on the covered dock (with adjustable louvers for inclement weather) and receptions in the climate-controlled Waterfront Ballroom with coffered ceilings and wood floors. Indoor seating capacity reaches 200 (300+ for events overall). On-site lodging totals 15 keys (11 main-building rooms/suites plus 4 one-bedroom waterfront cottages), with amenities including a dedicated Bridal Cottage, Groom's (Waterfront) Suite, outdoor swimming pool, complimentary made-to-order breakfast, bicycles, kayaks, paddleboards, and on-site gourmet catering by Chef Dave Donohue.


