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Great Oak Manor

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10568 Cliff Rd, Chestertown, MD 21620
Special Price
August Mid-Week BOGO
Great Oak Manor
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Ranked #5 of 12 Chestertown B&B and Inns
A recent review
5 of 5 stars Reviewed June 22, 2009
TeamVA Fairfax, VA
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167 Reviews from our TripAdvisor Community

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Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    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
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There are newer reviews for Great Oak Manor
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Fairfax, VA
Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed June 22, 2009

Our bicycling group of ten reserved 5 rooms at the Inn and we were blown away with the Inn. It is in a beautiful setting just outside Chestertown, MD. We were biking in the area and wanted a quiet place to stay that would allow us to gather for social times after riding. The Inn has beautiful grounds, patios to... More 

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Wading River, New York
Level Contributor
3 reviews
5 of 5 stars Reviewed June 1, 2009

Our family stayed for one week and celebrated our daughter's wedding there. It was just perfect. We have gotten so many compliments from our guests saying it was the best wedding ever - we certainly believe so. Our hosts John & Cassandra and their staff could not do enough for us - make sure you ask for Charlie. The rooms... More 

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New York
1 review
5 of 5 stars Reviewed May 27, 2009

I was very impressed with my overall experience at the Great Oak Manor. The house is absolutely beautiful, the grounds are breathtaking and the owners Cassandra and John are most hospitable. The staff is warm, friendly and accommodating as well. We were at the Great Oak Manor for my cousins wedding and took over the Inn with family and friends.... More 

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Freeport, Maine
1 review
5 of 5 stars Reviewed May 10, 2009

We arrived at this charming and secluded bed and breakfast inn on the first of three consecutive rainy days. On our first morning, we asked the owner what he'd recommend we do on a rainy day. "Stay here!" he said with enthusiasm. "It's a manor house and you don't get to stay in a place like this very often, so... More 

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Philadelphia, PA
2 reviews
5 of 5 stars Reviewed April 12, 2009

My wife and I aren't usually impressed by luxury and pampering, but this vacation was one of those times where we really needed some down time and a nice place to spend it. The Great Oak Manor really delivered on all counts for us. We reserved The Tilden Room which is on the second floor with an awesome view of... More 

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Delaware
Level Contributor
40 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 42 helpful votes
5 of 5 stars Reviewed April 6, 2009

I won a trip to the Great Oak Manor at my Hotels annual Christmas party several years ago. I have to admit I have never stayed at a bed and breakfast before, but I have toured through many of them. I work at a luxury hotel which is typically reffered to as an oversized B&B, but the Great Oak Manor... More 

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Wichita, KS
1 review
5 of 5 stars Reviewed March 25, 2009

John and Cassandra are the consumate hosts. They and their staff will see that you have a very enjoyable experience at the Manor. I have stayed there multiple times and am never disappointed in the accomodations, food, or service. The rooms are comfortable and spacious. The view of the River/Bay is beautiful and the grounds very relaxing. An ideal place... More 

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Maryland
1 review
5 of 5 stars Reviewed March 25, 2009

You get a combination of the old fashioned feel of the 30's and touches of modern day. The staff is very professional, beds are comfortable and the grounds are beautiful. I love the staircase, each sitting room and little, clean beach with the beautiful white driftwood! Will definately stay again!

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Monrovia, Maryland
1 review
5 of 5 stars Reviewed March 20, 2009

Most of all we like the location and the beauty of the manor house. The manor house is located on a hill overlooking the Chesapeake Bay. There are many waterfowl and birds including Canada Geese and eagles. The manor house is grand and also warm and inviting. The warmth and hospitality of the home and the owners are also enhanced... More 

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Florida
Level Contributor
11 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed March 16, 2009

To be snowed in at Great Oak Manor Inn is a memorable stay at a B"nB. March 2, 2009, eleven inches of snow fell on the Eastern Shore of Maryland. My husband & I had returned to this inn for a birthday celebration a way from Florida! After the scrumptous breakfast we lounged in the beauty and quiet of the... More 

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