The well-appointed waterfront inn rooms and cottages at The Oaks offer romantic luxury and exceptional comfort. We also fulfill every need with thoughtful amenities and attentive service. Do as little or as much as you would like. For instance, you can relax on our Adirondack chairs and take it all in from a private veranda, or wander the lush grounds.
Our circa 1748 Waterfront Inn offers different sized rooms – some with Queen beds and some with King. Furnished with antiques, all rooms feature modern bathrooms, some with jetted bathtubs. Many of our rooms feature gas fireplaces seasonally. All rooms also include irons and ironing boards, hairdryers and toiletries. Our ADA compliant luxury waterfront cottage boasts a large bathroom, living room, kitchenette and king sized bed. Forget something? Inquire at the front desk. Daily housekeeping is provided.
Every morning brings stunning views of Oak Creek. And also a hot breakfast with seasonal fresh fruit, homemade croissants, and a choice of a savory or sweet hot entrée, such as French toast, savory pancakes or omelets sure to leave you with no room for lunch. Enjoy your breakfast in the dining room, or take a cup of coffee out to the terrace for a better view of the creek. We also offer complimentary beverages in the living room area.
Come relax in the tranquil beauty of Maryland’s Eastern Shore and the gracious hospitality of The Oaks Waterfront Inn!
Swim in our pool, bicycle on our beach cruisers, putt on our greens, and enjoy crabbing and fishing off of our private dock. Experience the beautiful sunset while canoeing in peaceful Oak Creek, an inlet of the Miles River. Enjoy a game of shuffleboard, badminton, horseshoes, or volleyball.
Or, simply enjoy a glass of wine waterside in one of our Adirondack chairs. Great Blue Herons, Ospreys, and transient Canada Geese are frequently spotted from our shoreline. Occasionally, we experience a Bald Eagle sighting!
Experience the Chesapeake Bay onboard the national historic landmark the Rebecca T. Ruark. Hoist the sails, steer to an oyster bar and dredge for oysters as you learn about the bay from a 3rd generation skipjack waterman – the infamous Captain Wade!
Harriet Tubman Tours | harriettubmantours.com 1.866.642.7743
Harriet Tubman Tours provides insights about the life and legacy of Harriet Tubman and surrounding History. All of their guides completed the same training given to rangers of the Harriet Tubman National Monument and State Park. In addition to knowing Harriet’s story, they are well-versed in the history and lore of the region.
Patriot Narrated Historical Cruises
Book on-line! patriotcruises.com
Experience waterfront St. Michaels on the Eastern Shore of Maryland aboard the Patriot. The 65-75 minute scenic river cruise is a delightful experience for all ages. Amenities include free parking, on-board bar and refreshments, indoor air conditioned spaces, a large, upper outdoor deck, and on-board bathrooms.
THE OAKS ROMANCE PACKAGE
Spend the night in one of our Deluxe Rooms with a king bed, whirlpool tub and fireplace (in season). Upon arrival at The Oaks you will receive a bottle of sparkling or white wine, a $100 gift certificate to Bistro St. Michaels Restaurant, a Chef selected miniature pastry platter and a delicious multi-course breakfast the next morning made by our renowned Chef. Pricing starts at $400 (plus tax) per couple.
*Two night minimum stay may be required on weekends*
*This is a weekday rate. Please call for weekend rates*
A Bottle of… $25 – $35
Choose a bottle of our house white wine or sparkling to compliment your stay. Sparkling cider also available.
Cheese Platter $35
A variety of different cheeses paired with assorted crackers are the perfect complement to a relaxing evening.
Miniature Pastry Platter $25
Our Chefs Assortment of delectable pastries and cookies will be waiting in your room when you arrive.
Picnic Lunch $24 pp
Our Chef will prepare the perfect picnic lunch packaged in a cooler bag with ice brick to keep. Please provide your order 24 hours in advance.
This enchanting Inn is the perfect getaway place to stay for a few days of rest and relaxation.
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. The inn keeper was very friendly and welcoming. I felt like I was visiting family. I will be returning soon.
Friendly atmosphere, quaintness, excellent service. The breakfast was wonderful, the grounds were beautiful, the room was amazing, the fireplace was a nice surprise. Stayed an extra day.