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Great Oak Manor

10568 Cliff Rd, Chestertown, MD 21620
Great Oak Manor
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150 reviews from our community

Traveler rating
    130
    13
    4
    1
    2
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12
90
6
5
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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Delaware
Reviewer
4 reviews 4 reviews
5 of 5 stars Reviewed 1 week ago

Great Oak Manor has incredible views of the Chesapeake Bay. There's access to a small beach, which our dog loved! (No extra fee for bringing her! 2 dog-friendly rooms available) The manor is charmingly decorated with comfortable arm chairs and couches, the breakfast was great, and the rooms well appointed. We stayed Friday and Saturday, off-season, so the rates were... More 

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Top Contributor
59 reviews 59 reviews
36 helpful votes 36 helpful votes
4 of 5 stars Reviewed February 28, 2015 via mobile

We arrived to find to our surprise that our visit coincided with the first day under new ownership. Jenn, the inn manager that others have raved about, remains the innkeeper and was unfailingly helpful and cheerful. The house is nicely located with a beautiful view of the bay, and the sunset each evening over the water. There are several communal... More 

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Jennifer D, Manager at Great Oak Manor, responded to this review

We're glad you enjoyed your time at Great Oak Manor and that you also got to share your visit with the new owners' first weekend! You really made the weekend special by being their first official guests. It was a pleasure meeting you both and we hope you return to see all of the new improvements that we have already... More 

Wallingford, Pennsylvania
Reviewer
3 reviews 3 reviews
5 of 5 stars Reviewed January 17, 2015

My favorite place in the world to paint and watch birds. Amazing staff, best breakfast I've ever had at a B&B worldwide. Best view. Can't say enough nice things about the character of the building, furniture, library and did I mention VIEW! Eagles, kingfishers, herons, warblers, turkeys, etc. Binoculars provided! Can't say enough nice things about the Inn, Innkeeper, staff,... More 

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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
339 reviews 339 reviews
73 hotel reviews
265 helpful votes 265 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 

Was this review helpful? Yes 2
Jennifer D, Manager at Great Oak Manor, responded to this review

Hi Judy, We were sorry to hear you had a disappointing stay with us back in October 2014. We wanted to write in response with a few updates and comments. We are now currently under new ownership (since February) and have been working on giving each room the attention they need cosmetically, along with updating the modern features to better... More 

Minneapolis
Top Contributor
105 reviews 105 reviews
102 hotel reviews
132 helpful votes 132 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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philadelphia
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
Reviewer
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 

Was this review helpful? Yes 1
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