A Waterfront Eastern Shore Hotel
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.
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.
We’re proud to offer an award-winning restaurant located in town. Bistro St. Michaels provides an exceptional dining experience for our guests and the public alike.
Celebrate in Style at The Oaks
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.
The property is entirely yours when you book a wedding. Let The Oaks and its grounds become a private place for you and your guests to enjoy a memorable celebration.
Our lavish event space in Maryland, various breakout locations and expansive outdoor space, create a quintessential setting to fulfill your agenda or celebrate your special occasion.
No detail at our renovated St. Michaels, MD hotel and event venue has been overlooked. Our sense of serenity and comfortable sophistication makes us an ideal place to get away from it all.
“I have been traveling across the country for the past 30 years, and I can honestly say that this was the most memorable lodging experience that I’ve ever had.”
and Romantic Atmosphere”
“Our guests raved about the beautiful location, scenery, amazing service and romantic atmosphere”
with The Oaks”
“From the first time we walked through the front door – we were enamored with The Oaks and all of the staff”
“All of our guests were beyond impressed with the venue, service and quality. It could not have been a more perfect weekend for us”
Enhance Your Stay
When your world closes in on you, plot an escape to ours. See our special offers and ideas to enhance your stay.