Great Oak Manor

10568 Cliff Rd, Chestertown, MD 21620, USA

Address:	10568 Cliff Rd, Chestertown, MD 21620, USA
Phone:	+1 410-778-5943
Site:	greatoakmd.com
Rating:	4.8

Location

Photos 100

Reviews 10

Unique Person

Loved it is exactly right! On our way back from Washington DC. to NYC it was getting late so we decided to sleep somewhere. As I wanted to see more of the countryside I googled a bit for something off the beaten track and found this hotel. We called up and yes, it took two calls to be connected to the right person that told us that a room was available. I am so glad I made that second call - the Hotel is lovely and very special. A beautiful old manor was converted with lots of taste into a hotel that lets you feel as if you truly were the guest of one of the squires of old. Each one of the 12 guest rooms (ours was more of a suite) has its own name and tasteful decor. The manor sits on sprawling grounds overlooking the water, you can watch squirrels play and birds of all kinds soar while sipping tea on the terrace. But I have to say what I loved most was the wonderful and very personal service of the innkeeper. She was extremely friendly and helpful, making us feel welcome and taken care of not with the usual professionally friendly but somewhat interchangeable demeanor of regular hotel staff but as a real person. Great Oak Manor is not one of your faceless hotels that revel in cooky cutter amenities. It feels as if stories could and would happen here - and if you are somebody who likes the individual and personal this is definitely the place for you.

Jessica R

My family and I recently stayed at Great Oak over a winter weekend. I dont have enough positive adjectives to describe both our stay and the Chestertown/bay area itself. First off, the view is unbelievable. Right when we arrived, we got to watch the sun set by the edge of the bay. There is a beach area where we ended up getting some incredible photos of the sunset. The Inn is within a few minutes driving distance from town, so it was really convenient to get back and forth from the restaurants for dinner & sightseeing. We had our breakfasts at the inn which was home cooked and delicious (cinnamon buns were a favorite)! The grounds were really well-maintained, even for it being cold/snowy. Before our visit, I was heavily leaning towards a wedding venue closer to my hometown in Pennsylvania, but after our stay, Ive decided to book at Great Oak. Really excited to go back again when its warmer and tour more of the rooms and see some of the updates that they were working on during the winter.

Rachel Cumberland

My now husband and I stayed at Great Oak Manor for our wedding night on Sept. 19th. A lot of our guests also stayed at the manor during the weekend. Everyone only had amazing things to say about the rooms, estate, and the new staff! Scott & Kaylin were absolutely wonderful throughout the whole wedding planning process, especially since the manor switched owners from when we held the rooms for guests and the wedding weekend. There was never a hitch in any planning. Scott & Kaylin also helped us out when we forgot to get the key to our room before the wedding -- the one detail I forgot, thankfully! I would 100% recommend the Great Oak Manor to anyone looking for a relaxing and lovely stay on the Eastern Shore!

Paula Teller

My father is 93 and an amazing artist who takes me on a week long painting trip somewhere in the world every year. From New Zealand and Bermuda to Germany, England and Frances Rue de Vin. But our all time favorite trip was at the Great Oak Manor in Chestertown, MD. Everything exceeded our expectations from the quaint historic furniture, the beautiful sunsets, the eagles, the homemade baked goods and the wonderful conservatory where we could paint when raining. But we believe it was the hospitality of the Innkeeper and staff that also has us ranking this as our favorite Inn in the world. They were so thoughtful and considerate of me and my fathers needs that we have been back every year since!

Sasha Mairs

We rented out the carriage house for my boyfriends birthday and it was worth every penny. We had a full kitchen bigger than mine at home, we only used the refrigerator, but did make use of their grill. The bed was comfortable and the sheets were so nice! But by far the most exciting part was the bathroom, a clawfoot tub and three shower heads in the walk in shower, it was so cool. We were treated like family by the innkeepers, (a sweet southern bell and good old southern gentleman). They had a home made sausage for breakfast that was amazing, my only complaint was that I only got it one morning since every day breakfast was different. Finally someone set off fireworks

Ashley Stough

The manor was fantastic. The service and food were phenomenal and I had a very wonderful experience. My room was the Geddes-Piper also known as the "bird watching" room on the third floor and it was very comfortable with its own adjustable heating. The bed was probably the most comfortable bed, similar to temperpedic. The innkeeper was extremely accommodating when booking and the view was gorgeous from the house and the beach area. I would highly recommend to anyone who would like a nice getaway and great food. Unfortunately we didnt get to utilize the bikes and kayaks, but we definitely will come back at a warmer time.

susana ash

Just wonderful! Gorgeous property and grounds on the bay. Access to swimming pool and fitness room in an adjoining property. Kayaks, canoes and paddleboards available for guest use. We went with 2 teenagers and had a beautiful suite. Holly and Richard were very accommodating to our various dietary needs - 2 vegans and one celiac. The breakfasts were topnotch and creative . Will definitely make this our go to in the Chesapeake area. Also, they regularly run specials - we took advantage of a buy one night, get one night free deal that was running through August. The kids were additional but still a bargain.

Eileen R

I just returned from a wonderful stay at the Great Oak Manor Bed and Breakfast and it was so relaxing. The view and sunset was spectacular! I really enjoyed learning about the Inn’s rich history. Apparently, the new owners have made many improvements in and around the Manor. The period furnishings lent to the Inn’s rich history and were very comfortable. The rooms were spotless. The Innkeeper was very friendly and happy to satisfy your every request. She served a fabulous breakfast and served dinner upon our request. You truly feel like youre a special guest in someones home. Cant wait to visit again!

Dana Healy

Our visit to GOM was fantastic. The innkeepers, Kaylin and Scott, were accommodating, personable and professional. We saw bald eagles on the property as well as many other birds. My husband enjoys bird watching, he noted the golden finches, Hawks, and many cardinals. He wore his "bird watching gives me cheep trills" shirt all weekend and the innkeepers were nice enough to not mention it. The view is spectacular and our whole stay was relaxing. We will be repeat customers.

Jim Gorman

My wife and have stayed at Great Oak Manor for two weekends last month. It is a beautiful place top to bottom. Quiet, stately, great grounds, attentive staff, water front views, breakfast to die for, wonderful rooms and other amenities. Port and sherry with the afternoon treats. The services and staff are friendly and simply the best. We plan to go back any time we need a treat.