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“Great View, could use updating” 3 of 5 stars
Review of Great Oak Manor Inn

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Great Oak Manor Inn
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10568 Cliff Rd, Chestertown, MD 21620   |  
Hotel amenities
Ranked #5 of 12 Chestertown B&B and Inns
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
“Great View, could use updating”
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I say this not being a huge B&B person, but I thought that the Inn was a bit outdated.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
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143 reviews from our community

Traveler rating
    126
    11
    4
    1
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See reviews for
11
86
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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 (14)
Date | Rating
  • English first
  • Any
English first
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
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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
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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
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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
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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
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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
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Annapolis, Maryland
2 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed November 16, 2011

My wife and I can't say enough great things about the innkeepers Cassandra and John, and their staff. We would run out of superlatives. They all contributed to making my birthday celebration a memorable one. If you get a chance, visit them once, and you will be hooked for life.

Room Tip: Ask for the corner suite in the back of the manor.
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  • Stayed November 2011, traveled with friends
    • 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.
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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 ( Wi-Fi ) 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): $$
Number of rooms: 11
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

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