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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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Washington, D.C.
Senior Reviewer
6 reviews 6 reviews
2 helpful votes 2 helpful votes
4 of 5 stars Reviewed November 8, 2014

My parents and I spent a lovely weekend at this property where they had stayed some years prior. They had often talked about it so I was excited to finally visit. The room we stayed in was on the first floor to accommodate my mother's mobility issues and it was a large bedroom with a king for them and a... More 

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New Jersey
2 reviews
5 of 5 stars Reviewed November 6, 2014

Simply wonderful! Jen and her team (she is a new innkeeper) make the Manor all that much of a one of a kind experience. The manor echoes with history whether it is the detailed wood carvings above a fireplace to the stories of gambling. The grounds are large enough to find your own little hideaway and enjoy the scenic views.... More 

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Owings Mills, Maryland
Top Contributor
299 reviews 299 reviews
64 hotel reviews
220 helpful votes 220 helpful votes
1 of 5 stars Reviewed October 27, 2014

We were very excited about visiting the Great Oak Manor which is in Select Registry folio. We have been to a lot of these properties and have NEVER been disappointed until now. I usually do not do “Pros and Cons” but this is the best way to explain. CONS: 1) The wi-fi was down all weekend and phone coverage was... More 

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Top Contributor
96 reviews 96 reviews
93 hotel reviews
125 helpful votes 125 helpful votes
5 of 5 stars Reviewed October 11, 2014

Stayed at the Great Oak for 3 nights on Womantours Maryland Eastern Shore bike trip. Loved it. Innkeeper Jenn was very welcoming, the accommodations were superb and the breakfasts were spectacular (so glad I was biking every day so I could enjoy the food to the max). Stayed in the 'Caulk' room. 2 single beds that appeared smaller then a... More 

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Senior Reviewer
6 reviews 6 reviews
4 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed September 24, 2014

Spent 4 days and 3 nights at this lovely inn and thoroughly enjoyed our visit. The quaint town, Chestertown, was the location for many of our activities but we were able to visit other communities and see quite a bit of history of the region. Returning to the inn in between and preparing for dinner was the special treat. Breakfast... More 

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New York City, New York
4 reviews 4 reviews
4 hotel reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 20, 2014

My husband and I escaped to Great Oak Manor for a quick three day mini-moon after our wedding. Everything about our stay was perfect! The manor is beautiful, the food is delicious and the hospitality is exceptional! It was the perfect spot to sleep late, read on the grounds all day (and spot bald eagles in the trees just over... More 

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Baltimore, Maryland
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 7, 2014

I had heard about Great Oak Manor for years, but only recently had the opportunity to plan a trip myself. It was a little difficult to find(could use better signage) but it was well worth the backtracking. The manor itself is a gorgeous movie set like building, and the interior is decorated in an elegant,if faded charming way. However, the... More 

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McLean, VA
11 reviews 11 reviews
7 hotel reviews
12 helpful votes 12 helpful votes
4 of 5 stars Reviewed July 23, 2014

We have returned to Great Oak Manor again and again. It's peaceful, quiet and uplifting. Rooms are well decorated and comfortable. The grounds are fantastic. There's not tons to do in the area so bring your bikes and fishing poles but mostly get ready to relax.

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Sparks, Maryland
5 reviews 5 reviews
5 hotel reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed June 20, 2014

My wife and I spend a lot of our leisure time at B&B's and Inns, especially the Select Registry ones, and we both just loved this place ---- right on the water, beautiful grounds, fabulous common rooms, bald eagles and ospreys all about; just wonderful. The innkeeper, Jen, was just delightful; very warm and engaging, but always with an eye... More 

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Top Contributor
77 reviews 77 reviews
7 hotel reviews
40 helpful votes 40 helpful votes
5 of 5 stars Reviewed June 16, 2014

We had lived in Maryland for a long time but had never been to Chestertown, just on the other side of the Chesapeake Bay and north from the Bay Bridge. Our children gave us a gift certificate to Great Oak Manor Inn for our anniversary last year, and we finally got a chance to use it. Great Oak Manor is... 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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