The Perfect Escape

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!



or book online


Main House guest rooms range from $150 to $300 a night (a full breakfast is included in the room rate). Please call 410-745-5053 for more details. Visa, Mastercard, American Express, Discover, Cash or Check are accepted. A 6% Maryland sales tax and 4% Talbot County Room Tax are applied to all room tariffs.
Call us for guaranteed lowest rate at 410-745-5053. Reservations are guaranteed with a major credit card.
Check In & Check Out
Check In : 3:00p.m. to 5:00p.m.
Check Out: 11a.m.
If you are planning to arrive after 5:00 p.m., please call the front desk to make late arrival arrangements. Please check out by 11:00 am.
A credit card is required to guarantee your reservation. If booking through a third party, please make note of their cancellation policy. Room deposits are fully refundable if cancellation is made 30 days prior to arrival, otherwise initial deposit can be placed towards a future date with a $50 rescheduling fee. 
Breakfast is served daily. Please let us know of food allergies and intolerances.
Although The Staff of The Oaks Waterfront Inn loves pets, some of our guests do not share the same affections. We are unable to allow pets at The Oaks but are happy to provide you with some great boarding options in the area.
Additional Policies
The Oaks Waterfront Inn is a smoke free facility. Smoking is permitted outside the Inn. Rooms are based on double occupancy. We can arrange for air mattresses and breakfast for any additional guests. Charges for additional guests vary based on age.
Restaurant Facilities
Breakfast included daily.

Local Activities

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!


Skipjack Cruise


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!

(Seasonal Availability)

Harriet Tubman Tours |  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!


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 Waterfront Inn & Events Maryland Wedding Venues Room Cottages and outdoor event spaces

Enhance Your Stay


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.