Easton, Maryland
Easton, Maryland

A Waterfront Eastern Shore Hotel

Seating area with fireplace at hotel in St. Michaels MD

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.

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Entry door to Cottage 1 at Maryland waterfront inn
Double vanity in Waterfront Suite bathroom vertical
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.

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The Oak Room main dining area
The Oak Room Restaurant & Bar

This winter, the Oak Room offers a full menu Tuesday – Thursday from 4:00 pm to 9:00 pm welcoming you to indulge in an unforgettable dining experience at one of the best waterfront venues in the area.

The Oak Room Menu & Calendar

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.

Newlywed couple celebrating in The Oaks ceremony garden
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.

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Table of women laughing and celebrating private event at The Oaks
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.

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happy couple laughing and riding bikes at The Oaks in St Michaels
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.

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Two glasses clinking together by the water
Young couple holding hands and walking to the pool
“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.”

Derek–Booking.com

“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

Featured Specials

The Suite Life
Book any of our suites and enjoy 25% off the last night of your stay. *2-night minimum required.
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Spontaneous Getaway
Feeling spontaneous? Book a stay the same week of your arrival and enjoy 20% off the last night.
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Stay a Little Longer
Enjoy 25% off the last night of your stay when you book 3 or more nights.
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private cottages with waterfront views in St Michaels MD