The Perfect Escape

The well-appointed waterfront inn rooms and cottages at The Oaks offer romantic luxury and exceptional comfort. Thoughtful amenities and attentive service assure every need is fulfilled. Do as little or as much as you would like. Relax on our Adirondack chairs, take it all in from a private veranda, or wander the lush grounds.

Our circa 1748 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 are equipped with 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 is not only met with stunning views of Oak Creek, but 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. Complimentary beverages are offered 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!


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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 are treated to a Bald Eagle sighting!

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


Main House guest rooms range from $110 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. Cancellations should be made 1 week prior to your stay (2 weeks for Cottage) or you will be charged for one night’s stay if we are unable to rebook.
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.
Please inform us of your cancellation at least 1 week prior for guest rooms, 2 weeks prior for the cottage.
Breakfast is typically served at 8:30 a.m. on weekdays and from 8:30 to 9:30 on the weekends. We will make every effort to accommodate other times with advance notice. 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.  Lunch Sandwich Menu available for our guests.

Enhance Your Stay & Specials


Midweek Getaway

Enjoy two or three nights in one of our Queen Rooms and gourmet breakfast each morning made by our Award Winning Chef. Pricing starting at two nights for just $350 or three nights for $495 (plus tax)

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 champagne or white wine, a $100 gift certificate to Award Winning 208 Talbot Restaurant, a chef selected miniature pastry platter and a delicious multi-course breakfast the next morning made by our renowned chef. $350 (plus tax) per couple. (Two night minimum stay may be required on holiday weekends; subject to availability at time of booking.)


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.

Skipjack Cruise $35 per person
(Seasonal Availability) 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!

The Oaks Waterfront Inn & Events Maryland Wedding Venue 2017 Guest Review Award