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All 11 Chestertown B&Bs / inns »

Great Oak Manor Inn

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 119 Reviews
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119 reviews from our community

Traveller rating
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Families
8
 
Couples
68
 
Solo
4
 
Business
4
 
What travellers say
  • Chesapeake Bay(17)
  • Fresh fruit(5)
  • Perfect hosts(3)
  • Music room(3)
  • French toast(3)
Date Rating
Allentown, PA
Senior Reviewer
8 reviews 8 reviews
Reviews in 5 cities Reviews in 5 cities
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed 13 May 2012
1
person found this review helpful

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... More

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John Fedas, Owner at Great Oak Manor Inn, responded to this review
28 May 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... More

1 review
5 of 5 stars Reviewed 26 March 2012

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... More

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Reviewer
4 reviews 4 reviews
Reviews in 3 cities Reviews in 3 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 18 March 2012

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... More

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Beaverdam, Virginia
1 review
5 of 5 stars Reviewed 5 March 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... More

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Contributor
11 reviews 11 reviews
Reviews in 8 cities Reviews in 8 cities
7 helpful votes 7 helpful votes
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... More

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Annapolis, Maryland
2 reviews
Reviews in 2 cities Reviews in 2 cities
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. More

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Washington DC, District of Columbia
1 review
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... More

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Newark, Delaware
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
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... More

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Princeton, New Jersey
1 review
1 helpful vote 1 helpful vote
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... More

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Arlington, Virginia
Senior Reviewer
8 reviews 8 reviews
Reviews in 7 cities Reviews in 7 cities
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 12 August 2011

We only stayed at the Inn for one night, but it was a great evening! John and Cassandra were great hosts and the INN is a very lovely setting. More

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Additional Information about Great Oak Manor Inn

10568 Cliff Rd, Chestertown, MD 21620
Price range (per night):* 169 AUD - 318 AUD

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