We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

“Outstanding Property and Location” 4 of 5 stars
Review of Great Oak Manor

We can't find prices for this accommodation
Our online travel partners don't provide prices for this accommodation, but we can search other options in Chestertown
Check In mm/dd/yyyy Check Out mm/dd/yyyy
Great Oak Manor
Save
You added Great Oak Manor to your Saves list
10568 Cliff Rd, Chestertown, MD 21620   |  
Hotel amenities
Ranked #6 of 12 Chestertown B&B and Inns
Savannah, GA
Senior Contributor
47 reviews 47 reviews
33 hotel reviews
Reviews in 36 cities Reviews in 36 cities
23 helpful votes 23 helpful votes
“Outstanding Property and Location”
4 of 5 stars Reviewed July 31, 2012

Great river views from room and expansive lawn in the back of a beautiful manor house. Spacious and comfortable room. Good staff...very accomodating. Ten minutes away from cute town with good restaurants. Would go back.

  • Stayed June 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Write a Review

151 reviews from our community

Traveler rating
    131
    13
    4
    1
    2
See reviews for
12
91
6
5
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    4.5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (17)
Date | Rating
  • English first
  • Any
English first
West Friendship, Maryland
2 reviews
5 of 5 stars Reviewed July 30, 2012

My husband and I stayed at the Inn for our 2 yr Anniversary. Jenn the Inn keeper made us feel right at home! When we got to our room we found a bottle of champagne with a little note telling us Happy Anniversary and enjoy our weekend. We took that bottle down to the water and enjoyed the views and sat on the beach area. It was like our private evening on the bay!The breakfast each morning was so good with all the homemade goodies! Our bed was so comfy neither of us wanted to get up but we were glad we did! Jenn helped us pick restaurants each night and her recommendations were perfect! We loved it so much we already booked another weekend to go back!

Room Tip: Highly recommend D'Oench
See more room tips
  • Stayed July 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Philadelphia, Pennsylvania
Senior Contributor
25 reviews 25 reviews
8 hotel reviews
Reviews in 12 cities Reviews in 12 cities
17 helpful votes 17 helpful votes
5 of 5 stars Reviewed July 30, 2012

From the moment we drove up to this beautiful manor we were impressed. The innkeeper, Jennifer, was gracious and welcoming. We had a romantic stay in the Marmaduke with the most incredibly comfortable bed I have ever slept on. [If I could have fit it into my suitcase I would have!] The next morning we were served a delicious french toast casserole that I am still craving. Long talks on the lawn facing the water with the soft sounds of breaking waves only added to our experience. And I did I mention the Tiki Bar at the marina was walkable from the grounds?!? No need to drive.
Synopsis: Breath-taking manor home. Slept like a dream. Ate like royalty. Returning soon.

Room Tip: Go for the Marmaduke if you want the best bed in history.
See more room tips
  • Stayed July 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
New York City, New York
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
2 of 5 stars Reviewed July 29, 2012

We expected a clean B&B, but no. The main house is attractive, but the room assigned to us was incredibly dusty with icky carpet in the bathroom. We asked to be shown another room and ended up in a room with NO air conditioning and NO working television. All this for $200+ per night. We have stayed in the Brampton Inn in Chestertown, and the only reason we tried this inn instead was that the Brampton was sold out. Now we know why!

  • Stayed June 2012, traveled with family
    • 1 of 5 stars Value
    • 3 of 5 stars Location
    • 1 of 5 stars Sleep Quality
    • 2 of 5 stars Rooms
    • 1 of 5 stars Cleanliness
    • 3 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Concord, Massachusetts
Senior Contributor
21 reviews 21 reviews
5 hotel reviews
Reviews in 8 cities Reviews in 8 cities
11 helpful votes 11 helpful votes
4 of 5 stars Reviewed July 16, 2012

Spent 2 nights at the manor midweek. Gorgeous grounds, and view. Gracious staff. Amanda greeted us, Jennifer gave us great suggestions for things to do and places to eat. Loved the Blue Crab sunset Cruise in Rock Hall, and eating at the Kitchen there for lunch. Loved Mount Harmon Plantation, another suggestion. Generous breakfast with personalized service. Nice afternoon snacks as well. Impressive manor with a sweeping central staircase. Downstairs is very well cared for. Some updating needed in our room. Stayed in the RingGold. High ceiling, king size bed, and generally comfortable. The bathroom floor needs updating (Carpeting should be replaced by tile.) outdoor chairs On the lawn the chairs needed to be replaced, and were removed our second day, with new ones ordered. We were in the area for a wedding and would return again if vacationing near Chestertown. Great for peace and quiet and beauty.

  • Stayed July 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Baltimore, Maryland
Reviewer
5 reviews 5 reviews
Reviews in 5 cities Reviews in 5 cities
4 helpful votes 4 helpful votes
4 of 5 stars Reviewed July 9, 2012

We traveled to Great Oak for a 2-night getaway. We chose it for the location--on the Eastern Shore near Chestertown and Rock Hall, and because it is right on the water. The view is excellent,as we had hoped, and the overall setting is very nice. Beautiful grounds, peaceful setting. We had a very nice experience. We were greeted by Amanda, who gave us a great welcome and introduction to the Inn. The Inn was quiet and comfortable, with the amenities we like--dvds to borrow and watch in the room, good snacks in the afternoons and cold drinks available all the time. We also liked that there were beach towels and water shoes available, though we did not use them this trip. Breakfast was good enough, and pleasantly served. Our room was clean and comfortable, and large compared to other places I've stayed. We lucked out and got one of the new mattresses--GREAT investment--we slept very well. Next investment should be a new shower head. I agree with some of the other reviews that there are aspects of the decor that need to be updated, but that will not keep me away. I will come back to enjoy the peace and quiet, the beautiful view and grounds, a large, comfortable room, and the friendly but unobtrusive staff. As mentioned by others, upon the suggestion of the innkeeper we tried the blue crab charters sailing trip--this was a lot of fun and a good deal. Great suggestion.

  • Stayed July 2012, traveled as a couple
    • 3 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Clarksville, MD
Reviewer
3 reviews 3 reviews
3 hotel reviews
Reviews in 3 cities Reviews in 3 cities
6 helpful votes 6 helpful votes
1 of 5 stars Reviewed June 8, 2012

We stayed in mid-week for a getaway in May. The Inn was under new management and the new innkeeper was trying to be helpful and friendly, so that was appreciated but not enough.
The view and grounds are nice, but as a prior review said there was no beach. (Fortunately there was no boating or yacht noise when we were there. The marina is very close so I can see that would be a problem.) When we arrived there was no one in the house at all. We finally found an open door but were there a while before anyone came.
The bedroom we stayed in was a bit dated in decor, but the worst thing was the truly awful mattress - I tossed and turned for two nights and left with a back ache. The second night we were there, the air conditioning came on at full blast at 4 am - rattling the vents and making the room so cold and noisy we could not sleep. We told the innkeeper the next day but there was no explanation or apology.
The food at breakfast consisted of nice hot homemade muffins but we were only given one tiny one each, and the rest of the food was awful - very dry and crumbly eggs one morning.
The home itself was once grand but I could not find a piece of upholstered furniture that was not severely stained and lumpy - no where to sit and be comfortable.
So, a bed and breakfast severely lacking - don't waste your money on this place.

  • Stayed May 2012, traveled as a couple
    • 1 of 5 stars Value
    • 4 of 5 stars Location
    • 1 of 5 stars Sleep Quality
    • 2 of 5 stars Rooms
    • 3 of 5 stars Cleanliness
    • 2 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Hotels you might also like...
mm/dd/yyyy mm/dd/yyyy
Price Your Stay

Been to Great Oak Manor? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Great Oak Manor

Address: 10568 Cliff Rd, Chestertown, MD 21620
Location: United States > Maryland > Chestertown
Amenities:
Bar / Lounge Beach Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Pets Allowed ( Dog / Pet Friendly ) Suites
Hotel Style:
Ranked #6 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $$$
Number of rooms: 12
Official Description (provided by the hotel):
Great Oak Manor is located on Maryland's Eastern Shore, where the Chesapeake Bay is aglow in vibrant, warm sunsets; where towering oaks gently kiss the skyline; and where you can let your body rest and your mind wander. Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century country-style estate rests alongside the Chesapeake Bay waterfront. With 12 guestrooms and various common rooms, Great Oak Manor offers the finest in a romantic luxury bed and breakfast inn, where all of your whims are cared for, day and night. Whether you're adventurous, need to get away, or just want to be taken care of, there's something here for everyone. Spend an afternoon perusing the quaint streets of historic Chestertown, exploring the Eastern Neck Refuge, sampling the fresh catch in Rock Hall, or just curl up in the arms of a weathered Adirondack chair to soak up the view. Aside from offering a relaxing getaway for travelers, Great Oak Manor also serves as the ideal location for various events, retreats, parties, and weddings. Welcome to our home, stay a while. ... more   less 
Also Known As:
Great Oak Manor Hotel Chestertown

Owners: What's your side of the story?

If you own or manage Great Oak Manor, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.