The Oaks Waterfront

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!

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!

Outstanding boutique hotel on the water. Everything is new. Staff is fantastic. Lovely romantic weekend there

We were greeted with the warmest reception.by Linda. The new renovations accentuates the natural surroundings of the inn, making it very hard to leave. The staff are very accommodating to your needs and helping to plan your daily adventures.

What a venue! My family stayed on the premises for our daughter's wedding. Everything was absolutely amazing!!! It had been totally renovated over the winter and it couldn't have been lovelier! The main building was decorated beautifully, and the event space was great. The only complaint I had was the dance floor was a little small. The majority of our guests danced all night long and were dancing next to the tables because the floor couldn't fit them (there were just under 140 guests). The food was excellent from the cocktail hour (served outside along the water and on the covered dock) to the dinner (served inside the renovated space). The waitstaff and bartenders were friendly and attentive. The entire bridal party stayed on site either in the main building or in the four brand new cottages that were just built. The cottages were perfect! The bridal cottage had a row of makeup mirrors and chairs, perfect for the girls to get ready at. The owners really thought of everything. I would be remiss if I didn't give a shout-out to the folks who ran the show...Lamonde, Joe, Linda and Cassidy. What a team! They treated us like family from the moment we arrived and helped make this wedding weekend truly exceptional. I can't even list all the extra things they did to make our stay worry-free (like sending shuttles into town to pick us up after a night of dinner and drinks, and storing our food for the after-party in their commercial fridge - thanks Chef!) They provided bikes for our pleasure and were always available for anything that came up. I would recommend this venue to anyone looking to host anything in this part of Maryland...it can't be beat for customer service, beautiful surroundings, and an awesome, capable staff. I'm already thinking of coming back for a family reunion or vacation stay. Thank you all!!

Going to Sait Micheals Md. was a birthday treat for my husband. We stayed in a junior suite, so it was not inexpensive. However, the place is beautifully done with top notch staff. It has recently been renovated in a very tasteful manner and the grounds are beautiful. The only food service is a free breakfast which was always very good. The weather did not cooperate so we could not enjoy the outside portions of the building which are also beautiful. They do many weddings, and it is a perfect spot for that venue. We had no complaints at all except that there were no glasses in the room. (A minor point that management should easily take care of)

Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!

Wonderful stay at the Oaks. The property was renovated within the past year and the grounds and rooms are extraordinary. The area was very tranquil, enjoyed the pool and kayaking in the creek and the tasty breakfast. The staff were very pleasant and Linda was a wonderful host. Looking forward to returning.

Our stay at the Oaks at Waterfront was wonderful. The hotel has gone through a major renovation and is absolutely beautiful. The staff were so helpful and friendly. No hesitation that we are coming back for another visit. Stay in this little gem of a inn in the St Michael’s area.