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.

“Not worth the money” 1 of 5 stars
Review of Great Oak Manor Inn

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 Inn
Save Saved
You added Great Oak Manor Inn to your Saves list
10568 Cliff Rd, Chestertown, MD 21620   |  
Hotel amenities
Ranked #5 of 12 Chestertown B&B and Inns
Clarksville, MD
Reviewer
3 reviews 3 reviews
3 hotel reviews
Reviews in 3 cities Reviews in 3 cities
6 helpful votes 6 helpful votes
“Not worth the money”
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.
Write a Review

142 people have reviewed this hotel

Traveler rating
    125
    11
    4
    1
    1
See reviews for
11
85
5
4
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    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 (13)
Date | Rating
  • English first
  • Any
English first
Washington DC, District of Columbia
Senior Reviewer
6 reviews 6 reviews
6 hotel reviews
Reviews in 6 cities Reviews in 6 cities
4 helpful votes 4 helpful votes
3 of 5 stars Reviewed June 1, 2012

The best thing about the Great Oak Manor is the view. It really is amazing and the property is huge. There are chairs to sit on, it did get a bit buggy so we couldn't sit out for long. They do provide bug spray which is nice.

The property itself is historic. The addition of the pool looked nice although we did not go in. They provide towels and shower shoes if you want to go in the Bay.

Housekeeping was great, our room was spotless. The towels in the bathroom were very nice.

Breakfast was sufficient. Fruit, cereal, yogurt, muffins and one other thing, one day it was a quiche, the other french toast. What was provided wasn't a lot but what they had was very good. They will make eggs to order but you have to ask for them.

We ran each morning on the road by the Inn. Traffic on it wasn't too bad and we saw a lot of deer.

There were a few downsides of the inn. There is no beach. There is a tiny strip of sand that is probably 4 feet wide by 10 feet long. You couldn't sit out there or enjoy it. When we walked down there were two random people drinking beer there. Part of the reason we booked the Great Oak was for the beach and were quite disappointed when we realized there was not one.

Another downside is that the Manor is right next to a yacht club that is open late with music. The music started around 7 or so and went until at least 1. You could not sit outside in the evening and enjoy the quiet because the music was quite loud. We could hear it in our room as well, but it wasn't loud enough to keep us awake.

While our bedroom was spacious, our mattress was terrible. We probably sunk a good 6 inches when we sat down. It was difficult to get up or move around on it. It really, really needs to be replaced. We stayed in the Marmaduke room.

I say this not being a huge B&B person, but I thought that the Inn was a bit outdated. The fake flowers everywhere were tired looking, the wallpaper in our bedroom was peeling, all the magazines were well over a year old, overall, the Inn was a bit tired looking.

Chestertown did not have much to see or do downtown. I would not go expecting you are going to spend a lot of time there. Our best part of the trip was taking a sail boat ride with Blue Crab Charters in Rock Hall. For $30 a person you get an hour and a half ride on the Bay. It was beautiful. It was by far the highlight of our trip. Rock Hall has a little more to see than Chesapeake, but not much. We went to the 'beach' there which was fine, saved by a great breeze.

I would probably not go back to Great Oak Manor Inn. While the view is indeed great, the price was very high and I do not think it was quite worth it.

  • Stayed May 2012, traveled as a couple
    • 3 of 5 stars Value
    • 4 of 5 stars Location
    • 3 of 5 stars Sleep Quality
    • 3 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.
Allentown, PA
Contributor
11 reviews 11 reviews
6 hotel reviews
Reviews in 7 cities Reviews in 7 cities
11 helpful votes 11 helpful votes
5 of 5 stars Reviewed May 13, 2012

We were saddened to learn that the inn would no longer be under your expert management, and want to let you know that we were glad that we were at Great Oak for the final weekend. It's been so wonderful visiting with you and John at the inn, and we will most certainly miss your outstanding service and the warm friendship you've extended to us again and again throughout the year. Take good care of your golden co-host, Charly. We will miss his happy greeting as well!

  • Stayed April 2012, traveled as a couple
    • 5 of 5 stars Service
Was this review helpful? Yes 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
GreatOakJohn, Owner at Great Oak Manor Inn, responded to this review, May 28, 2012
We were so honored you were there for our final weekend. Enduring relationships with our guests have made this 10 year experience precious to us. John and I want to thank you and everyone who has taken the time to write and share your experiences at Great Oak Manor on tripadvisor. It truly has been our pleasure to meet all of you and provide you with the gracious hospitality that we have always aspired to achieve.
We will miss all of you and wish you all the best.
Cassandra and John Fedas
Charly the golden
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewer
3 reviews 3 reviews
Reviews in 3 cities Reviews in 3 cities
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed March 26, 2012 via mobile

The gracious hospitality offered by Innkeeper Casssandra and her sweet golden retriever Charlie was rivaled onky by the jaw-dropping view from the back garden of this beautiful waterfront estate. The vibe is one of easy-going elegance, and every need and detail was attended to. We slept like babies, filled our bellies with yummy breakfasts, and our big lug of a dog Hunter was treated like a king. It was hard to leave.

  • Stayed March 2012
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 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.
Reviewer
5 reviews 5 reviews
Reviews in 4 cities Reviews in 4 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed March 18, 2012 via mobile

My husband and I just returned from a wonderful, rejuvenating long weekend at the Great Oak Inn. We were looking for a special place to celebrate our 26th wedding anniversary and this was just the spot. The Inn was magnificent and Cassandra and staff were most accommodating. Breakfast and snacks were very tasty. We had the Bay view to ourselves the first night and loved the spectacular sunset and quiet. We spent the day light hours exploring Chestertown, Rock Fall, and the Eastern Shore Wildlife Preserve. We had dinner at two completely different but spectacular restaurants. After breakfast this morning, we took a walk around the spectacular property and surrounding area. The hillside covered in yellow and white daffodils brought out the photographer in me. We headed home knowing that we will visit again soon!

Stayed March 2012
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Beaverdam, Virginia
1 review
5 of 5 stars Reviewed March 5, 2012

My husband and I were looking for a relaxing weekend and we got so much more! Our stay at Great Oak was a true retreat and a trip through time. The grandeur and stoic beauty of the estate is the perfect complement to the magnificence of its natural surroundings. The panoramic view of the water is hypnotic. The glittering history of Great Oak in its heyday gives you access to old world glamour. We truly felt transported and luxuriated in our room, which was both elegant and cozy. Our hosts, John and Cassandra, made us feel truly at home and ensured that we were taken care of yet also given the space to enjoy our down time. We are already planning a return trip!

  • Stayed February 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.
Contributor
20 reviews 20 reviews
9 hotel reviews
Reviews in 12 cities Reviews in 12 cities
12 helpful votes 12 helpful votes
5 of 5 stars Reviewed February 2, 2012

The Great Oak Manor is nestled in the woods with views of the Chester River. A warm welcome by the innkeeper Cassandra and her staff assured us of a great evening. The room was spacious, warm, and inviting. Cassandra took us on a tour of this grand establishment; a former hunting lodge. You could get lost in the spaciousness. Cassandra also took care of our dinner reservations without hesitation. We enjoyed a lovely evening at the Imperial Hotel in Chestertown. The food was perfect and the atmosphere quiet and cozy; just what we were looking for after a long day.
We were extremely comfortable at the inn and the amenities allowed us time to relax and enjoy the evening. Sherry or port is waiting for you in the living room; allowing you to relax and enjoy the evening even further. In the morning, coffee was waiting in the parlor and when we went down to the dining room we were met by John and Cassandra. A full breakfast is served; warm cranberry muffins, fruit, juice, coffee, and a hot dish. We were so full that we didn't stop on our journey home for lunch. All in all, our stay was wonderful. The room was very clean, the service fantastic; it had all the comforts of our own home. We will visit again!

  • Stayed January 2012, traveled with family
    • 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.
Hotels you might also like...
mm/dd/yyyy mm/dd/yyyy
Price Your Stay

Been to Great Oak Manor Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Great Oak Manor Inn

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 Swimming Pool
Hotel Style:
Ranked #5 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $$
Official Description (provided by the hotel):
Great Oak Manor on the eastern shore of the Chesapeake Bay is aglow in 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 waterfront. With 11 guestrooms, Great Oak offers the finest in a romantic luxury bed and breakfast inn. ... 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 Inn, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.