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Great Oak Manor

GreenLeadersBronze level
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10568 Cliff Rd, Chestertown, MD 21620
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1 room 1 adult
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211 Reviews from our TripAdvisor Community

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Fairfax, Virginia
1 review
5 of 5 stars Reviewed February 13, 2011

Should you choose to stay at the Great Oak Manor B & B on the Chesapeake Bay, you're in for a real treat !!! A girlfriend and I had a little mini escape to Chestertown, MD and loved every minute of it. Cassandra greeted us and gave us a tour of the inn. I must say, she is the most... More 

Helpful?
Thank lalonemom
Centreville, MD
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed January 4, 2011

Great Oak Manor takes guests back to an earlier, more gracious period. With a lovely setting overlooking the Chesapeake Bay one feels the peace of the estate immediately. We have stayed in summer and winter. Both are wonderful. The manor does not have dining facilities for dinner so this requires guests to drive anywhere from ten to thirty minutes to... More 

Helpful?
1 Thank ssb2Centreville_MD
BelAir
1 review
5 of 5 stars Reviewed January 2, 2011

Great Oak is not our first B&B but it is surely our favorite! Cassandra and John are the most wonderful hosts we have encountered. They have created a warm, generous, inviting environment. We felt like welcomed guests at a friend's home and look forward to our next visit! This B&B is a jewel to treasure, Chestertown a pleasure to tour,... More 

Helpful?
Thank jodi50
Bel Air, Maryland
1 review
5 of 5 stars Reviewed December 12, 2010

We have made many trips to Great Oak and have always enjoyed our stay. It is a beautifully quiet scenic setting on the water. The inn is beautifully decorated and welcoming. The food is always outstanding. John and Cassandra are perfect hosts and we feel like we are visiting old friends every time they welcome us to the Inn.

Helpful?
Thank traveler3437
Yardley, Pennsylvania
Level Contributor
5 reviews
common_n_hotel_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed November 19, 2010

It was time to get away from our daily lives! We made a call to the Inn, who graciously accommodated us, and set out on our journey. As we drove up the long oak lined drive, we were greeted by a beautiful manor, set right on the edge of the Chesapeake Bay. The Oak Manor Inn was built in the... More 

Helpful?
Thank prancingpeacock
Baltimore, Maryland
1 review
5 of 5 stars Reviewed November 17, 2010

My husband, retired military, surprised me with an evening at Great Oak Manor Inn B& B for Veterans Day 2010. He received the evening free in honor of his service. What gracious hosts! From the time we walked into the spacious entrance way, through the charming tour of the house and its many rooms and amenities, to our room, we... More 

Helpful?
Thank dachshundiva
Havre de Grace, Maryland
1 review
3 of 5 stars Reviewed November 13, 2010

Extraordinary remote site with a beautiful mansion, well appointed comfortable rooms, many accomodating common rooms. Particularly nice large glassed lounge between innkeeper's residence and guests' manor house. Innkeepers very friendly, non intrusive, almost like guests. Breakfast was exceptionally good and snacks available any time. Several nice local restaurants for evening dining. This experience was one of the nicest we have... More 

Helpful?
Thank Deanseen
Aberdeen, Maryland
1 review
5 of 5 stars Reviewed November 11, 2010

The Great Oak Manor was spectacular. Impeccable grounds and facilities and very gracious innkeepers. As part of a nationwide program, John and Cassandra opened their beautiful estate up to Veterans for a complementary stay last night. We had never been to a B&B and, as recent transfers to the Maryland area, had not ventured out to the Eastern Shore. What... More 

Helpful?
Thank kgcarric
Madison, WI
1 review
5 of 5 stars Reviewed November 5, 2010

This is a large, elegant, beautifully-furnished Georgian-style house run by two lovely people who were very helpful in every way. The breakfast was delicious and all four of us were more than satisfied with everything about our stay. The grounds are very pretty and the view of the Bay is great. This would be a wonderful place for a wedding.

Helpful?
Thank jheymann
Leonardtown, Maryland
1 review
4 of 5 stars Reviewed November 3, 2010

3rd visit(Spring, Summer and Fall); Great Oak is a grand, traditional manor house overlooking the Chesapeake Bay; The bedrooms are spacious, well decorated and furnished and many with lovely water views. The baths are comfortable and updated but don't expect a fine hotels marble walls and water pressure. The public rooms are individually decorated with tasteful effect and each come... More 

Helpful?
Thank pfnorton
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