Great Oak Manor

One of Maryland's historically significant estates, Great Oak Manor sits on twelve acres directly on the Chesapeake Bay in Maryland's Eastern Shore. With large common rooms and beautifully appointed guest rooms, comfortable outside... more

Visit the website for

Here is what guests had to say...

"Great Oak Manor" 11/9/2009
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 11/2009

Have just spent a wonderful week-end with friends and family at Great Oak. John and Cassandra were the perfect hosts. Staying in their beautiful home was a joy, the house was magnificent, and the views of the bay perfect. We recieved such wonderful attention from our hosts, from the moment we stepped into the front door. From food and drinks, and all the other extra details, would highly reccomend Great Oak for anyone looking for a quiet retreat.

View Reviewer Info


"Magical Wedding at Breat Oak Manor" 10/16/2009
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 9/2009

We chose to have our wedding and reception at Great Oak Manor. It was the perfect setting. Our family and bridal party stayed with us at the inn which made it very intimate. John and Cassandra were the perfect hosts. Infact, they were more like family. We hope to return every year for our anniversary!

View Reviewer Info


"Great Escape" 9/17/2009
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 6/2009

We just married off our only daughter and needed a retreat! Steve and I experienced the Great Oak Manor last year...so my search for the perfect B&B was over!!! Naturally, we headed to GOM for our get-a-way. We also celebrated our 38th Wedding Anniversary there! God willing, we will continue this trend for our Anniversary celebrations!!! Rita L.

View Reviewer Info


""C.H.A.O.S." " 3/25/2009
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 3/2009

We arrived in a caravan of cars and vans for our 12th consecutive annual weekend of pampering at the Great Oak Manor; we are welcomed like family coming home for a visit by John and Cassandra. We are a group of 15+/- ladies calling ourselves "C.H.A.O.S." (Crop Happy Addicts Of Scrapbooking) who gather yealy to relax and indulge ourselves the beautiful manor and surrounding grounds. We work on our scrapbooks, read, crochet, quilt, and just relax. This is the one weekend a year that is "ours" and we are spoiled and catered to all weekend long. We have come to look upon Great Oak Manor as our home away from home and when the weekend ends we are already looking forward to the following year.

View Reviewer Info


"Anniversary trip" 3/6/2009
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 2/2009

We recommend this Inn to anyone that loves great food, fine wine, terrific music, beautiful scenery, friendly innkeepers and luxurious spaces. We loved every minute!!!

View Reviewer Info


"elegant accomodations; super innkeepers" 2/8/2009
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 2/2009

We wanted a quiet, relaxing environment to escape and recharge our batteries. Great Oak Manor was all that an more. The innkeepers were unobtrusive but attentive to any way to make our stay more enjoyable. The accomodations are spacious and very well maintained. We regretfully left, refreshed.

View Reviewer Info


"astounding" 11/17/2008
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 11/2008

Such a beautiful place. All care is taken to make each guest feel spoiled. It's my new favorite B&B!

View Reviewer Info


"Pamper yourself - Visit Great Oak Manor" 10/2/2008
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 9/2008

Innkeepers John and Cassandra Fedas were so friendly and accommodations and made my visit so relaxing and comfortable. I didn't want for anything. I was able to relax and anjoy some quiet time as well as see the area! My visit was too short!

View Reviewer Info


"A Fabulous High Life Weekend at the Great Oak Manor" 7/23/2008
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 7/2008

Great Oak Manor is intimate, personal, and high end. If I told Cassandra that I wanted to have dinner at a particular place, she would dissapear and return with dinner reservations. Chestertown itself is a cool little college like town with a lot to offer, but I really wish I had a few extra days to stay in the gigantic mansion itself. You decompress at the Great Oak Manor, sitting bay side in a hammock with a glass of wine. The lap pool is fantastic, great way to start a morning before breakfast which you could eat in the dining room or out on the patio (which is where Cassandra would help you set up your day there) They delivered champagne to my room nightly with no issues and I was able to roam about freely in the massive site. Everyone met up around 7:00 each evening for port and sherry in the study which was such a pleasant plus to the experience. It's beautiful and it's relaxing and we are thankful we visited, as we will without question return to this site again and hopefully more sooner than later!

View Reviewer Info


"Memorial Day Weekend" 5/29/2008
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 5/2008

The Great Oak Manor is a great place to stay. The manor house is wonderful, with beautiful views and places to relax. The grounds are extensive with many places to take in the views of the Bay. The rooms are very comfortable and the hosts will pamper you. I can't wait to return.

View Reviewer Info


"My first time, will not be my last time" 5/26/2008
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 5/2008

Cassandra and John, my friends and I had a wonderful time at Great Oak Manor. We did not what to leave, but in our leaving we are truly inspired to spread the word of how wonderful our experience was at Great Oak Manor! The rooms were spacious and clean the private baths were huge and the grounds were breathtaking! Tonya Richardson

View Reviewer Info


"Great Oak Manor" 5/15/2008
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 3/2008

The Great Oak Manor provided a great getaway from a very busy life. The innkeepers were a delight. What an enchanting place. We would love to return.

View Reviewer Info


"What a relaxing retreat!" 4/30/2008
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 4/2008

We've had a wonderful week-long stay at the manor this april 2008. The location is gorgeous and the rooms absolutely lovely. Owners and staff went out of their way to make us feel at home. We highly recommend this B&B and would love to come back!

View Reviewer Info


"Great Oak Manor" 4/30/2008
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 3/2008

The Great Oak Manor provided a great getaway from a very busy life. The innkeepers were a delight. What an enchanting place. We would love to return.

View Reviewer Info


"A quiet, secluded retreat" 4/28/2008
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 4/2008

My husband planned a surprise weekend getaway to celebrate my special "milestone" birthday. He selected the Great Oak because it looked to be a wonderful secluded place to relax and get away from the hustle and bustle of our busy lives. The grounds, the scenery and the home and its surroundings were beautiful, and very peaceful. However, we were not as impressed by the service. Our initial impression when we first arrived was not what we expected. After being on the road for over 4 hours with the first 2 in heavy traffic, we were looking forward to a relaxing weekend getaway. The innkeeper welcomed us by telling us she was just sitting down to dinner, then rushed us through a hurried "tour" of the home. This made us feel uncomfortable the moment we walked through the door, because we were imposing. Feeling rushed is exactly what we were hoping to leave behind. During our 2-night stay, the housekeeping staff removed from our room our fine crystal champagne glasses we brought with us. We brought them from England and they were a discontinued pattern. We did retrieve them, however, they were unfortunately run through the dishwasher. The staff also removed some water bottles we planned to keep (we purposely left them on the table and did not discard them in the trash can less than a foot away). I think the housekeeping staff should leave the guests' personal belongings as they are. All in all, the Great Oak Manor was a lovely place. Being awoken by a chorus of birds in the morning was one of the highlights of our stay.

View Reviewer Info

Innkeeper Response
I was happy to read that you found your stay with Great Oak Manor Bed and Breakfast to be “all in all a lovely place”. Therefore it saddened me that I misread you on your arrival. It is our intention for our guests to feel at home. I am very sorry if I made you feel hurried or uncomfortable. Arriving frazzled during the dinner hour, perhaps you misinterpreted my intention in the abbreviated tour. Although most Bed and Breakfast Inns are the innkeepers home, we fully understand that it is a 24/7 responsibility. Dinner for us is usually a juggling act that we try to keep invisible to our guests. My elderly father also lives with us so we try to keep his meal on schedule. I am sorry I did not take the time to fully explain the situation. Most of our good local restaurants have their last seating at 8 PM and I wanted to insure you would get proper seating. Your enjoyment on your days spent here are up most on our minds and I would not have wanted you to spend it at a pizza parlor. I guess I should have taken a few minutes to explain all of this, I am sorry. As for the stemware that was removed from your room, sincerest of apologies are in order. We hope that you recognize that staff inadvertently removed these items not knowing their value to you and significance. They simply assumed that the glasses were ours as it is highly unusual for guests staying with us to bring such valuable and precious items. We do offer Anniversary Champagne on silver trays with champagne flutes. Our morning shift just did not realize they were yours. Our staff also mistook your empty bottles of water for ours since this is also offered complimentary. We have had a talk with all the employees so that they are more aware of personal items that should not be handled. I hope this brief letter helps to explain our actions and in some small measure retrieves the good name of Great Oak Manor Inn. I hope that sometime in the future you will return to a full measure of hospitality.

- Cassandra Fedas (innkeeper)

"Superior ambiance" 1/24/2008
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 12/2007

Restful, welcoming, friendly hosts. 5 star dinner. Elegant and tasteful.

View Reviewer Info


"Great Oak Manor." 12/12/2007
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 11/2007

Beautiful ocean view b&b on the eastern shore. Great Oak Manor is a beautiful and peaceful b&b. The house is elegant and majestic, and the view is spectacular, over the Chesapeake Bay. The rooms are comfortable and elegant with nice modern ammenities. Breakfast is delicious, especially the manor muffins.

View Reviewer Info


"We'll go again" 10/14/2007
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 10/2007

My wife and I have stayed at B&B's around the world and Great Oak Manor is right there with the best of them. Ask Casandra to help arrange a crab dinner on the back patio. It was great and we will return.

View Reviewer Info


"Great Place to Relax" 9/13/2007
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 9/2007

Our 4 day stay was absolutely relaxing. Beautiful surroundings, great host and hostess. Beat breakfasts, especially the crab quiche. We didn't want to leave! Helen & Joe

View Reviewer Info


"Beautiful and Relaxing" 9/2/2007
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 8/2007

This is the 4th time we stayed at Great Oak Manor and we will keep coming back. The house is gorgeous and every room has its own beauty and charm. The property itself couldn't be better as it faces the Chesapeake Bay as well as Fairlee Creek. What a wonderful place to come to relax and to revitalize yourself. The breakfasts are delicious and all the people are very friendly and helpful. What a total wonderful inn experience!

View Reviewer Info


"Annual Scrapbooking Weekend" 5/16/2007
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 3/2007

I am part of a scrapbooking group consisting of 12 to 16 women who all share the passion of working on our family albums. This past March we celebrated our 10th annual weekend at Great Oak Manor. Each year we all look forward to our weekend away from all the streses in our lives. We are greated each year with big hugs from John and Cassandra as they welcome us to their home for a weekend of pampering and relaxation. This is the highlight of our year.

View Reviewer Info


"Relaxing by the bay" 5/10/2007
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 4/2007

Just like the Otis Redding song "Sitting by the Dock of the Bay, the Great Oak Manor has perfected the art of getting away by the bay. When asked by friends to find something wrong with our three-night stay all we could think of was that it was too short. The elegant accommodations, gracious hosts, friendly staff and delightful cats resulted in an enervating restful stay. The breakfast each morning was first class with warm muffins, fruit, yogurt, and a full hot meal that varied for each day. Having a parlor, library, solarium (with giant hot tub), sun room, and lounge as common areas all with very comfortable furniture provided a wonderful surprise. The many chairs, hammocks, and chaise lounges doting the manicured lawn overlooking the bay was indeed a vacationer’s delight. Having access to the executive length golf club next door was a real bonus. Being able to watch bald eagles, osprey, blue heron, and numerous other birds rounded out a complete relaxing occasion. The Great Oak Manor is not just for special occasions but is worth the visit anytime you want to get away and relax.

View Reviewer Info

Innkeeper Response
Thank you so much for taking the time to write about your experience at Great Oak Manor. We are thrilled you enjoyed your stay and can't thank you enough for the wonderful review.

- Cassandra Fedas (innkeeper)

"A perfect weekend getaway" 2/4/2007
Overall
Rooms
Service
Value
Cleanliness
Dining
Stayed On: 2/2007

My wife and I make it a point to go somewhere special on our anniversary every year. We had never been to a B&B before. Cassandra (the owner & innkeeper) was abolutely delightful, and made the weekend very special. We were very pleased with our room, and enjoyed the fireplace on our late nights talks. The food was absolutely fantastic. We had a 6 course meal that ranged from salad w/ goat cheese to crab imperial and duck. The service was top notch. I have since recommended this place to several of my friends. I guess the one word that would describe this place is WOW!

View Reviewer Info


All reviews are the personal opinions of BedandBreakfast.com site users and do not reflect the views of BedandBreakfast.com.


Please share your comments with the millions of travelers who visit BedandBreakfast.com.

Contact Information


Great Oak Manor Bed and Breakfast
Great Oak Manor, Chestertown, MD - Inn
Great Oak Manor
10568 Cliff Rd
Chestertown, MD 21620-4115
USA
Phone: +1-410-778-5943
Fax: +1-410-810-2517
Toll-free: +1-800-504-3098
Innkeeper(s)
same as above
Rates:
$165 - $310
View Listing
Email Innkeeper
View Special Offers
View Recipes
Email to a friend
Travel gift certificate cards for B&B inns

BedandBreakfast.com

Nearby States:

1.Book Delaware inn bed and breakfast reservations and gift card certificates
2.Book District Of Columbia inn bed and breakfast reservations and gift card certificates
3.Book New Jersey inn bed and breakfast reservations and gift card certificates
4.Book Pennsylvania inn bed and breakfast reservations and gift card certificates
5.Book Virginia inn bed and breakfast reservations and gift card certificates
6.Book West Virginia inn bed and breakfast reservations and gift card certificates

Reviews

Overall
Guest Rooms
Service
Value
Cleanliness
Dining
Read all 23 reviews
Explanation of our ratings
Review Great Oak Manor, Chestertown, MD

Photo Album

Great Oak was built at a time when grandeur was more important than cost, when craftsmen were artisans and when houses were built to last for generations to enjoy. 

The Manor was built in the tradition of the 18th Century with bricks from the ballast of W.R. Grace sailing ships. 

A relaxing and memorable Bed & Breakfast on Maryland's Eastern Shore.A great getaway. The Chesapeake room is one of six common rooms available to our guest, for evening Port and Sherry, reading one of our 825 books, games, TV or movie watching, or simply relax by a winters fire.
The Conservatory, with west facing glass enclosure you can view the sunsets year round.Sitting with views of the bay, 
this elegant fireplace dining room features 
a full breakfast with Manor-baked muffins, hot entree, cereals, yogurts, and always fresh fruit.
   Welcome!
The Marmaduke Room - named for the first land grantee from Lord Baltimore overlooks the bay and is one of our deluxe waterviews with a king bed, sitting area, private bath and fireplace.D'Oench a deluxe waterfront room with king bed, fireplace expansive water views, sitting area, large private bath, and like all of our rooms equiped with luxury bathrobes hair dryers, irons and ironing boards. Come and relax.
Hodges, with a four posted queen, fireplace and large private bath is a great estate setting at a reasonable price.The Roese suite is two rooms. One with a king bed and writing area with desk. The other is a gracious living room with fireplace, sofa and sitting area with television and lots of light. The cathedral ceiling private bath and walk in closet add to this suites elegance.
The Roese suite is two rooms. One with a king bed and writing area with desk. The other is a gracious living room with fireplace, sofa and sitting area with television and lots of light. The cathedral ceiling private bath and walk in closet add to this suites elegance.