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Great Oak Manor Inn – reviews, photos

10568 Cliff Rd, Chestertown, MD 21620
Hotel amenities
Great Oak Manor Inn
Ranked #3 of 11 Chestertown B&B and Inns
5.0 of 5 stars 120 Reviews
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120 reviews from our community

What travellers say about this B&B/inn
  • Chesapeake Bay(17)
  • Fresh fruit(5)
  • French toast(3)
  • Music room(3)
  • Perfect hosts(3)
  • Delicious food(3)
  • Lounge chair(3)
  • Same time(3)
  • Private beach(3)
Traveller rating
    112
    4
    4
    0
    0
Only show reviews for Family (8) | Couples (69) | Business (4)
Date Rating
Contributor
11 reviews 11 reviews
Reviews in 9 cities Reviews in 9 cities
7 helpful votes 7 helpful votes
“The Perfect Getaway”
5 of 5 stars Reviewed 2 February 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, travelled 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
“Birthday Weekend”
5 of 5 stars Reviewed 16 November 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, travelled 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
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Ask Chip T about Great Oak Manor Inn
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Washington DC, District of Columbia
1 review
“Loved it! Cassandra was terrific!”
5 of 5 stars Reviewed 14 November 2011

I recently went to the Great Oak Manor for a "Mommy's weekend off" sponsored by my husband. We had been there together numerous times, but this time it was just me. I loved it, of course! My room was perfect... saw the eagle in the yard! Cassandra was warm and welcoming and confirmed for me, once again, that she runs an excellent inn. The weekend was exactly what I hoped for and I have her to thank. She made me feel like her home was mine, too.

  • Stayed October 2011, travelled solo
    • 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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Ask Beth W about Great Oak Manor Inn
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Newark, Delaware
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
“Savor the chance to be treated well.”
5 of 5 stars Reviewed 17 October 2011
1
person found this review helpful

Our dental group met here for 4 days. It was great in every way. The rooms were very comfortable and the prepared meals were the best I have experienced anywhere. Cassandra and John Fedas understand hospitality. Your need, expressed, is their next goal for accomplishing it. The entire time you feel extraordinary comfort. Cassandra accomplishes this with complete grace. She is the perfect hostess, consignier and sometimes "cook".The quiche (Lorraine or crab) (we had both at our request) are amazing. The portion size of all entrees was very large, and eaten by all with gusto.
Our members, due to airplane confusion, arrived and left at unusual times, yet Cassandra was there to help in anyway possible. She set out special meals and coffee for those leaving very early. She guided a lost traveler up to the Manor. She helped a large bus, who mistaken tried to enter the grounds...from getting stuck. She is there to help and she finds many ways to achieve this.
Give yourself permission to be totally spoiled.

Room Tip: Ask for Cassandra.
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  • Stayed October 2011, travelled on business
    • 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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Ask Carrietraveler_10 about Great Oak Manor Inn
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Princeton, New Jersey
1 review
1 helpful vote 1 helpful vote
“Great Weekend”
5 of 5 stars Reviewed 14 September 2011
1
person found this review helpful

We spent a lovely weekend at Great Oak Manor. The house sits on a bluff overlooking the bay and facing roughly west so the sunsets are beautiful. Most bedrooms face the water. The main floor has a series of livingrooms - 3 counting the music room, as well as a small garden room and a large reception hall between the old manor house and a newer residence for the owners. The reception hall faces bay and garden and is extremely pleasant. The house sits well back from the edge of the bluff on a graceful lawn with many lawn chairs - one can be alone or together easily. The lane the house is entered from is quiet and made for walks. On one side there is a quiet road with no outlet that also is nice for walks - it ends in a small park. On the other side is a marina and golf course. We did not use either but I assume that boats are rentable there and it makes a good destination for short bike rides. The beds and bedrooms are all generous, well lighted and comfortable, and well stocked with books. All decorations go with the general atmoshere of the manor - comfortable; not fussy. For meals there is a good selection of nearby restaurants in Rock Hall and Chestertown. A great place to visit!

Room Tip: Most rooms face the bay. About three do not, I believe, and the description of the rooms that do not...
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  • Stayed September 2011, travelled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Rooms
    • 5 of 5 stars Service
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Ask PJ11H about Great Oak Manor Inn
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Additional Information about Great Oak Manor Inn

10568 Cliff Rd, Chestertown, MD 21620
Price range (per night):* INR9,227 - 17,335

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