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All 12 Chestertown B&Bs / inns

Great Oak Manor Inn

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10568 Cliff Rd, Chestertown, MD 21620
Hotel amenities
Great Oak Manor Inn
Ranked #6 of 12 Chestertown B&B and Inns
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147 reviews from our community

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Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 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 Inn
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Wayne, Pennsylvania
Top Contributor
137 reviews 137 reviews
43 hotel reviews
91 helpful votes 91 helpful votes
5 of 5 stars Reviewed October 12, 2008

We have just returned from a one night stay at the Great Oak Manor outside of Chestertown. It is a beautiful place right on the Chester River and the folks there were so pleasant and helpful. We stayed in Caulk because of the small balcony but it was really hard to get a river view from it so we did... More 

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Millersville, MD
1 review
5 of 5 stars Reviewed October 11, 2008

We arrived at sunset on a Thursday night and were warmly greeted by the hostess. The sunsets on Maryland's Eastern Shore are breathtaking and this was no exception. Thoughtfully, the innkeeper said, "Just enjoy the sunset and I'll give you the tour when you are ready." We walked through the foyer and out the back door to the Chesapeake Bay... More 

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Oaks, Pennsylvania
1 review
5 of 5 stars Reviewed August 29, 2008

Our stay was absolutely wonderful! It is just what we needed.....alot of quiet and relax time. My husband and I stayed at the Great Oak Manor in Chestertown Maryland for a nice long weekend. We stayed 2 nites and left on Sunday morning. When we arrived we were greeted at the door and immediately you felt as if you were... More 

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Garnet Valley, pa
14 reviews 14 reviews
6 hotel reviews
9 helpful votes 9 helpful votes
5 of 5 stars Reviewed August 25, 2008

We have just returned from a relaxing and enjoyable weekend at the Great Oak Manor Inn on the Eastern Shore of Maryland. We travel to Bed and Breakfasts on a regular basis and this is one of the finest. The house is a reproduction of a Georgian manor home from the 18th century and has won architectural awards. It is... More 

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Senior Reviewer
10 reviews 10 reviews
3 hotel reviews
22 helpful votes 22 helpful votes
3 of 5 stars Reviewed August 21, 2008

We spent a weekday night here recently, just for a get-away. The Inn is beautiful, and the location, with a view of the Chesapeake Bay is stunning. Although the Inn is waterfront, it sits quite a bit back from the water, and the view is obscured by trees in many locations, especially from the rooms. It was a bit disappointing... More 

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Washington, DC
19 reviews 19 reviews
8 hotel reviews
18 helpful votes 18 helpful votes
5 of 5 stars Reviewed July 31, 2008

The innkeepers and staff at Great Oak Manor were helpful and lovely, and the inn itself is quite majestic. The public rooms are beautiful and plentiful and you often feel you have the run of the manor! Best of all, there's an incredible lawn behind the inn that provides a magnificient view of the Chesapeake Bay. Photos on the website... More 

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Arlington, VA
1 review
5 of 5 stars Reviewed May 29, 2008

Our family gathered at Great Oak Manor for a Memorial Day long weekend and a celebration of Veronica's birthday. We had a wonderful stay. The weather and the sunsets were beautiful. The rooms and the service were excellent. The grounds are just beautiful with views of the Chesapeake Bay. The hosts were great, friendly and engaging. I definately want to... More 

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1 review
5 of 5 stars Reviewed May 13, 2008

My husband and I are from the Sykesville area and thrilled to find such a wonderful and peaceful place in the elegant surroundings so close to our home. The grounds and Inn were beautifully kept, but not too stuffy. The inn keepers were very accommodating, but still gave us privacy. We enjoyed the grounds from sun up to sun down... More 

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1 review
5 of 5 stars Reviewed May 7, 2008

I experienced six fabulous days at Great Oak Manor Inn, and I cannot rave enough about everything: The facility and grounds are like a living fantasy, a mini castle on the Chesapeake Bay. The inkeepers are gracious, supportive, interesting/fun, and so very generous. The service is perfect. I look forward to returning again and again and to recommend it to... More 

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New Jersey
1 review
5 of 5 stars Reviewed April 17, 2008

I thought perfect didn't exist, but after visiting Great Oak Manor for 2 nights just recently, I might have to amend my thinking. The attention to detail is simply outstanding, the staff and owner couldn't be more friendly and accomodating, the manor itself is comfortable yet exquisitey furnished and maintained, and the setting overlooking the Chesapeake Bay makes you feel... More 

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Additional Information about Great Oak Manor Inn

Address: 10568 Cliff Rd, Chestertown, MD 21620
Location: United States > Maryland > Chestertown
Price Range (Based on Average Rates): $$
Number of rooms: 11
Also Known As:
Great Oak Manor Hotel Chestertown

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