Royal Oak, Maryland
Royal Oak, Maryland
Luggage on desk of luxury hotel and event venue in Maryland

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.

Elegant white bouquet by bedside at luxury hotel in St. Michaels, MD
Private cottage on the water in Maryland
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.

View Accommodations

Lamb chops at popular restaurant in Maryland
Savor Your Experience

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.

Bride and groom at waterfront wedding venue
Waterfront Weddings

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.

group of women with Champagne at group event
Private Events

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.

Covered dock at waterfront hotel in Maryland
Escape Your Everyday

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.

Bride and groom looking at fireworks in the sky at our hotel in St. Michaels
Seating area with chilled Champagne at our St. Michaels, MD hotel
“The Most Memorable
Lodging Experience”

“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.”


“Amazing Service
and Romantic Atmosphere”

“Our guests raved about the beautiful location, scenery, amazing service and romantic atmosphere”

Lisa–Wedding Wire

“We Were Enamored
with The Oaks”

“From the first time we walked through the front door – we were enamored with The Oaks and all of the staff”

Anonymous–The Knot

“Beyond Impressed”

“All of our guests were beyond impressed with the venue, service and quality. It could not have been a more perfect weekend for us”

Jessica–Wedding Wire

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.

Charcuterie Board
Enjoy a variety of cured meats, cheeses & crackers.
Eastern Shore Getaway
Relax with a 2-day escape to the Eastern Shore.
Romance Package
Revel in romance with your special someone.
Crabs & Drinks
Treat yourselves to a feast for the senses.
Picnic Lunch for Two
Savor a special chef’s selection for on-the-go enjoyment.
Water inlet at waterfront wedding venue and hotel in Maryland