The Oaks Waterfront Hotel

Excellent breakfast included

Just a warning. If you have a disability be sure to request a room on the first or second floor. The elevator only goes to floor 2. We had a lovely 3rd floor room which was no problem for us.

Beautifully renovated 1700s boutique hotel. Literally everything was well thought out when the new owners renovated it. Shuttle cars available to take you the 3 miles to St. Michaels. Chef breakfast included in your stay. Canoes/kayaks available. Can fish on the property. Wonderful staff who truly care about your stay. I will definitely be coming back!

10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.

Where to begin with this amazing stay? My husband and I went for a weekend to run the St. Michaels half marathon. We were looking for a quiet, relaxing place and the Oaks Waterfront surpassed our expectations. The property is impeccably maintained and, Linda, made us special early breakfast bags for the race since we would have to leave at 5AM, before breakfast service. She helped us find restaurants, get dinners, it was incredible. The property is so beautiful. We didn't bring our children but it would be a great place for them too!

My husband and I just returned from three nights at the Oaks, where we celebrated a few days away for our 25th anniversary. We cannot say enough wonderful things about our experience, from the warm greetings we received upon arrival and kindness and professionalism of everyone on staff, to the gorgeous (but casual) decor and stunning landscaping throughout the property and comfort of our beautiful room (we stayed in a junior suite). Oh, and those fabulous breakfasts! We found the Oaks by accident, had originally planned to stay at another lovely property down the road, but learned that the Oaks had been recently renovated and the pricing was equivalent, so we thought we'd give it a try. We made the right choice. Staying at the Oaks is not cheap, but it is an experience and that experience justifies the price. It's not a question of if we'll return, it's a question of when. It will definitely be again this year and we will stay in the same room. Thank you to everyone at the Oaks for a lovely anniversary getaway!

My wife and I have been trying to get to the Oaks Waterfront Hotel for some time and finally had the chance to visit during a last minute get away. We were very happy that the hotel was able to accommodate us at the last minute. After visiting the Harriet Tubman Museum and Educational Center (highly recommended BTW) that morning, we arrived at the hotel and were greeted warmly. We had requested a regular room but were upgraded without asking to a Junior Suite at the same cost, a very nice and unexpected surprise. The suite was gorgeous and very large, with nice views of the cove just beyond the deck outside of our room. The entire hotel was very beautiful as my wife kept commenting. The recent remodeling was very evident. That evening we enjoyed a quiet enjoyable dinner in the nicely appointed restaurant while gazing out at the cove. As we were finishing our meal, we were asked when we would want to eat breakfast so the chef would be ready for us. That also was an unexpected surprise. When we came down for breakfast the next morning. We were promptly served a delicious breakfast by a very friendly server. Sadly, we had to leave that day, but we hope to return again soon. I should add, as others have commented, that this hotel is a wonderful venue for a wedding.

The Oaks provided us with a fantastic experience for our weekend getaway. While the property caters to a number of weekend weddings, if you can snag one of its fewer than 20 rooms (or stop by Sunday-Thursday), you’re in for a great time! The whole hotel is brand new- the rooms, bathrooms, lobby, bar, and outside areas sparkle and are well decorated. Outside there is plenty of deck and lawn space, as well as a whole covered dock to lounge on. Inside, the lobby has a cozy fireplace and bar area to relax in. Rooms are large, bright, and our shower/bath was fantastic. As you would expect from a small boutique hotel, service is attentive and personal. The hotel manager Joe is a jack of all trades on property and goes out of his way to make you feel at home. To add to the convenience and experience, The Oaks has its own black car to drop off and pick you up from St. Michaels and other local destinations- a perfect way to get to and from dinner. Would highly recommend and we look forward to visiting again!

Beautiful facility and grounds and friendly staff.

Beautiful property, loved it!

Staff was extremely friendly and personable.