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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 #5 of 12 Chestertown B&B and Inns
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142 reviews from our community

Traveler rating
    125
    11
    4
    1
    1
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11
85
5
4
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (13)
Date | Rating
  • English first
  • Any
English first
New York City, New York
Reviewer
4 reviews 4 reviews
4 hotel reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 3 weeks ago

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
McLean, VA
Contributor
11 reviews 11 reviews
7 hotel reviews
11 helpful votes 11 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.

Was this review helpful? Yes 1
Sparks, Maryland
Reviewer
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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Maryland
Top Contributor
75 reviews 75 reviews
7 hotel reviews
39 helpful votes 39 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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Glenn Dale, Maryland
1 review
5 of 5 stars Reviewed May 27, 2014

My wife and I celebrated coming her coming home from Iraq at Great Oak. Immediately, we decided we wanted to have our wedding here. Even 4.5 years later, we are still amazed with the location. Thanks.

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Rising Sun, Maryland
1 review
4 of 5 stars Reviewed May 25, 2014

We celebrated a birthday and tea party weekend at the manor. It is a very impressive architectural example in beautiful surroundings with a wonderful view of the bay. We stayed in the Caulk room which was fine but I was mislead by the website describing a private terrace on which you can enjoy a sunset cocktail. It is more of... More

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Washington DC, District of Columbia
Reviewer
5 reviews 5 reviews
3 helpful votes 3 helpful votes
4 of 5 stars Reviewed November 15, 2013

We had three wonderful days at the inn. The room had a beautiful view of the Bay and the grounds were gorgeous and great for walking. On the day we left, we saw a pair of bald eagles. We stayed in the D'Oench room, and had a great bed. It felt too soft at first touch but we slept very... More

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Philadelphia, Pennsylvania
Senior Contributor
49 reviews 49 reviews
13 hotel reviews
20 helpful votes 20 helpful votes
5 of 5 stars Reviewed August 30, 2013

Ok, not really, but seeing 4 bald eagles on the estate at Great Oak Manor was just as exciting for us! My husband chose this spot for us, needing a getaway. Long ago, he yacht sat for some older friends at the marina there and would go up to the Manor's hammocks to read and relax on land. They were... More

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Hemel Hempstead, England, United Kingdom
Reviewer
4 reviews 4 reviews
4 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed July 24, 2013

After driving for 6 hours from NYC and arriving late at night we were greeted by a very friendly lady. We were meant to stay in a different suite but they were having troubles with the shower so she gave us a free upgrade. The manor was stunning and peaceful she gave us a small tour and told us we... More

Was this review helpful? Yes 1
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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): $$
Also Known As:
Great Oak Manor Hotel Chestertown

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