Great Oak Manor      
10568 Cliff Rd, Chestertown, MD 21620-4115, USA    
  • Free Night Participating Inn
 
 
Innkeeper/s:

Scott Benfield, Kaylin Benfield

Description

Circa 1938. This elegant Georgian mansion anchors vast lawns at the end of a long driveway. Situated directly on the Chesapeake Bay, it is a serene and picturesque country estate. A library with fireplace, den an...

Get a Free Night at this inn

The dates this property will honor the certificate are Nov. 1-March 31, Sunday-Thursday, gold rooms only.

- One Night Free: This property is featured as participating in the iLoveinns.com Buy-One-Night-Get-One-Night-Free program.


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Home away from Home

Dear Cassandra and John, The Great Oak certainly reflects the love and care you have given it over the years. We wanted a comforting, relaxing retreat from the hectic craziness of our daughters wedding. We were blessed with much more. Thank you for the warm welcome, the friendly banter, scrumptious breakfasts and a taste of home away from home. We wish you all the best. Thank you again for a lovely getaway.
Claire V
10/16/2011

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (1 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Our Wedding and Anniversary

We had been guests at Great Oak Manor a few times when we decided to get married in the beautiful inn. Our family joined us for the weekend. Our ceremony took place in the library and then we all enjoyed a wonderful catered dinner in the Conservatory. We returned recently to celebrate our 5th anniversary and enjoyed a beautiful sunset and a bottle of champagne by the Chesapeake. The innkeepers are the best! They take such great care of their guests - we really feel like a part of the Great Oak "family". Many thanks for providing some of my best memories! If you are looking for romance ... head to Chestertown!
Karyn Otte
Akron, OH
5/3/2010

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (1 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Phenomenal!

Our third visit; and second in six months! Beautiful, friendly, peaceful, relaxing. Top quality EVERYTHING! John & Cassandra make their guests feel like family.
Mike & Heike Weppner
Gainesville, VA
3/30/2010

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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Relaxing and Romantic

My husband and I stayed for our five year anniversary. It was better than our honeymoon! The food was outstanding. The room was perfect. The hosts, John and Cassandra, felt like old friends. We loved relaxing in the library in front of the fireplace at night with our port and sherry. It was outstanding. We look forward to returning.
Carrie Jonsson
Westminster, MD
3/20/2010

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (1 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Romantic

We had a great stay at Great Oak Manor..the setting, the room, the ambiance, the hosts, the food, the dog!
Ron S
Kensington, MD
2/28/2010

My ratings for this property      
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     Cleanliness
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Most romantic inn

Great Oak Manor Inn was one of the most romantic, most beautiful and inviting inn ever. The host, John & Cassandra were very warm. The fireplace of our room added to the ambience. Riding up to the grand manor and walking in the front door makes one gasp at its beauty. The food was absolutely delicious - the Valentines Dinner was wonderful, the desserts to die for. Breakfast was amazing, there was so much food! The french toast was truly the best I have ever had and elegantly presented. Snacks, fruit, sherry, gourmet cheese & crackers were offered everyday as well as cookies and sodas. John & Cassandra know how to make this one of the best couple of days of your life.
Susan Nagel
2/22/2010

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Our anniversary

We stayed at the Great Oak Manor last year for our anniversary. Loved it! Great food including a special wine-pairing dinner and very romantic.
Judy R
Norfolk, VA
2/12/2010

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Long Awaited Honeymoon

We are from Colorado but family lives in the Baltimore area so we were married at the Milton Inn in Baltimore. We wanted a place to go just for one night and found the Great Oak Manor on the internet. This was March so there weren't many people staying but we were treated with great warmth. We sat in front of the fire in our room and in the library and enjoyed the quiet, together. When you finally find your soulmate there is no more romantic place to start a life together than Great Oak Manor. We have been back for 2 anniversaries.
violette G
2/12/2010

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Magnificent!

We were engaged, married and celebrated our one year anniversary at the Great Oak Manor! Now our friends and family are fans of this magnificent manor as well. Dana & Brian
Dana Grafft
2/12/2010

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Perfect romantic setting

My dream place for a romantic getaway. Each room is elegant and comfortable. The solarium is a wonderful surprise for a B&B. The Various sitting rooms were available for casual relaxation or reading. The View from the outside sitting area was amazing especially in the evening when the sunset was at its best. A boater's delight with the adjoining marina.
Cochran J
Frederick, MD
2/2/2010

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Fabulous Inn

The most wonderful inn! Gorgeous rooms, fabulous breakfasts and amazing lawn. The Inn Keepers make you feel right at home.
Susan L
1/30/2010

My ratings for this property      
     Location
     Comfort
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Romantic

My husband and I have stayed at Great Oak Manor many times, in each of the seasons. It is a magical get-away with the utmost consideration for your comfort. Meals have been delicous, sophisticated and bountiful. We cannot wait to return.
Alma Hays
Baltimore, MD
1/30/2010

My ratings for this property      
     Location
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

The perfect weekend getaway

As a last minute decision, I decided to take my husband away for the night. It was a long weekend so I took advantage of the reduced Sunday rate. My husband is a history buff so I looked for a place with a story. I found it and more at the Great Oak Mannor Inn. Even though it was cold outside, inside there were fireplaces (including our room), port and Innkeepers that truly cared about our comfort. And the food, John made the most delicious crab cakes for dinner and breakfast was made to order...yum! The view is amazing, the food wonderful.
Devon H
Woodbridge, VA
1/20/2010

My ratings for this property      
     Location
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Relaxing honeymoon

Great Oak Manor Inn was the perfect setting to relax in after the whirlwind that is a wedding. With beautiful views of the bay, rustic decor, and excellent service this was the perfect end to a crazy weekend.
Katie Woge
8/4/2009

My ratings for this property      
     Location
     Comfort
     Condition
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Professional

The charming setting, professional service and personal warmth we experienced at Great Oak will long be a pleasant memory. Thanks for everything!
Anonymous
10/21/2008

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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

At A Glance

15 Review(s)
93% would stay again
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Publicity and Press Reviews

Southern Living, Philadelphia, Diversions, Road Best Traveled, Washingtonian, Country Inns, New Choices, Chesapeake Life, Time Magazine., Today Show with Peter Greenberg, July 2005.


Discussion

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