Easton, Maryland
Easton, Maryland
Patio table with umbrella overlooking river on the Eastern Shore

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.

Stack of muffins at Eastern Shore bed and breakfast
Savor Your Stay

Your day starts with a hot gourmet breakfast, served in our Breakfast Room between 8:30 and 9:30 am. We also provide a variety of add-on enhancements to enjoy on property, like wine, sweet & savory treats, and even a crab feast. Other dining options encompass a wide range of excellent restaurants just a short ride away in St. Michaels & Easton.

Property Attractions

Natural beauty abounds on our waterfront estate. Great blue herons, ospreys, and transient Canada geese are frequently spotted from our shoreline. Occasionally, we’re treated to a bald eagle sighting! You’re invited to lounge by the pool, sit at the bar, explore our property, and use our complimentary bikes, kayaks or paddleboards.

Chesapeake Bay beach shoreline
Fun Fact

During the early 1900s, one of the last silent films, “The First Kiss”, was filmed in Easton. The stars of the film, Gary Cooper and Faye Wray stayed at the inn during filming. Faye Wray was married on a skipjack on the Miles River while making the movie.

History of the Oaks

black and white photo of The Oaks

Origination of The Oaks

The fascinating history of the recently renovated Oaks Hotel dates back to the 17th Century. The Hotel resides on property from an original land grant deed to the Benson family by Lord Baltimore in about 1680. The entire plot of land consisted of 740 acres. A 42 acre portion of that property, where the Hotel now sits, was sold to the Harper Family in 1884 for $5,900. They farmed the land and it became known as Oak Hall.

Frederick Harper and his wife, Louise, started running the Hotel as a boarding house in 1902 to help with the expense of the farm. Guests would travel by steamship from the Western Shore to nearby Claiborne and catch the train to the hotel. The Harpers sold the farm in 1971 to the German Company Schwaben International who continued to run the Hotel as a corporate resort and cultural conference center.

renovations on waterfront hotel

The Quality Continues

In 1996, a St. Michaels couple purchased and completely renovated the Inn. In the winter of 2005, the Inn underwent a second major renovation adding on a large ballroom on the water side of the Inn. Since then, The Oaks has served as a premier waterfront venue for wedding receptions – where every moment is unforgettable.

Under new ownership in 2022, the Oaks began its most substantial renovation to date, with no detail left unturned. Renovations include soundproofed rooms, a new bar, new flooring, an elevator, waterfront cottages and many other luxury additions. The Oaks looks forward to celebrating your special moment, in an exclusive setting, with dedicated professionals, ensuring a relaxing and memorable event at our luxury St. Michaels, MD hotel.

bikes in front of cottages at luxury lodging in Easton Maryland
Blue ceramic decor at waterfront MD inn
Table with wine and flowers overlooking Eastern Shore water
Water inlet at waterfront wedding venue and hotel in Maryland