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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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Great Oak Manor
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211 Reviews from our TripAdvisor Community

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Stevensville, Maryland
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 3 weeks ago

We had our 4th Annual Half Way to Spring Fling this weekend and we had a wonderful time. The innkeepers were outstanding. We felt completely at home, the manor was spotless. Our room (The Caulk Room) was gorgeous, the bed was so comfortable with a beautiful view of the bay. So excited that they are making additions to the already... More 

Helpful?
Thank MLebling
Pittsburgh, Pennsylvania
Level Contributor
35 reviews
14 hotel reviews
common_n_hotel_reviews_1bd8 10 helpful votes
3 of 5 stars Reviewed 3 weeks ago via mobile

The GOM is a nice place but we got caught up in some convoluted pricing structure. I ended up paying over $200/night for myself solo. Going rate in the Chestertown area is less than $100. I am sure better place in summer as really no amenities in winter. Becomes a bed and shower which is available for much less at... More 

Helpful?
Thank Douglas S
Lutz, FL
Level Contributor
9 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed 3 weeks ago

What a beautiful and serene bed and breakfast. So regal feeling and yet so homey and relaxed. We had a wonderful time. everything was very clean and updated and beautifully decorated for the holidays, as well. Breakfast was delicious and very nicely presented. We will be back some day. Thank you!

Helpful?
Thank Nightengale106
Lancaster, Pennsylvania
Level Contributor
32 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
1 of 5 stars Reviewed 4 weeks ago via mobile

The worst part of our stay involves an incident with our car. The parking area was dark and inadequate for the number of cars. We were forced to park in the grass in front of those concrete blocks you see in parking lots. However, what we did not know and could not see due to absolutely no lighting, was that... More 

Helpful?
1 Thank MHeras
Maplewood, New Jersey
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 4 weeks ago

I'm sorry we could stay only one night. From the moment the hospitable innkeepers greeted us to the beautiful view of the sunset to the fabulous breakfast--the best B&B breakfast I've ever had--all of our needs were met (and many were exceeded). Although we did not have a room with a water view, we were not disappointed; the grounds are... More 

Helpful?
1 Thank Megan H
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Megan, Thank you so much for your kind words, we truly appreciate it. We are so thrilled to know that you enjoyed your stay. Please do come back and visit us in the warm weather! Kaylin Benfield Innkeeper More 

Philadelphia, Pennsylvania
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 4 weeks ago

We just spent New Years weekend at the Great Oak Manor. We had been looking to go somewhere away from the hustle and bustle of the city to relax and unwind. We thought the Eastern Shore was a good place to look. After doing our research, we found the Great Oak Manor. We were impressed by the website and decided... More 

Helpful?
1 Thank CallmeAL123
Wilmington, Delaware
1 review
5 of 5 stars Reviewed December 22, 2015

My dogs and I travel regularly for dog competition events, but I always hesitated to try a B&B. I was afraid the close quarters would be a challenge, and worried about being self conscious if my dog barked..At Great Oak Manor, we felt welcomed, comfortable and almost instantly felt at home. Everything is so spacious, and beautiful. Scott and Kaylin... More 

Helpful?
Thank Lynne Y
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Lynne, It was a pleasure to meet you as well as have you and your furry companions! We loved seeing a few of their tricks and were a pleasure. It is great to hear that you enjoyed your stay and felt right at home as that is certainly what we strive for each and every one of our guests.... More 

Boston, Massachusetts
Level Contributor
11 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed December 19, 2015

My husband and I had a wonderful experience while staying at this gorgeous B&B. The owners were incredibly friendly and accommodating. We only spent one night, but they let us linger throughout most of the following day, enjoying the beautiful grounds and the spectacular sunset on the Chesapeake. We arrived late at night and were delighted to find that they... More 

Helpful?
Thank KrystenF
GOMStaff, General Manager at Great Oak Manor, responded to this review

Krysten, Thank you so much for your kind words. We are so happy to know that you enjoyed your stay and were able to take full advantage of our wonderful property. It was a pleasure to have you as our guests and we hope that you'll come back and visit us again soon. Kaylin Benfield Innkeeper More 

Alexandria, Virginia
1 review
5 of 5 stars Reviewed December 1, 2015

Lovely large house with wide grounds and stunning view. We felt quite welcome. Especially good for those with dogs. The house is about 15 minutes from Chestertown which is where you'd go for dinner. Google maps misdirected us so its best to get directions directly from the inn.

Helpful?
Thank Alexposter
GOMStaff, General Manager at Great Oak Manor, responded to this review

We are so thrilled to hear that you enjoyed your stay at the Manor and were able to take advantage of the grounds to roam! It is always a pleasure to know that our guests feel welcome and comfortable as that is what we strive for. We hope to have you back again soon. Kaylin Benfield Innkeeper More 

La Plata, Maryland
1 review
5 of 5 stars Reviewed November 26, 2015

We stayed at the Great Oak Manor two nights, November 21st and 22nd. We (3 couples) stayed at the manor while taking advantage of a guided duck hunt on the eastern shore on the 22nd. When we arrived, we were greeted by Scott and he provided us the tour of the beautiful manor and grounds. The rooms were fabulous, filled... More 

Helpful?
Thank Terrie H
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Terrie, Scott and I do appreciate your kind words. It was such a pleasure to have yourself and your group in house and we are very pleased to know that you enjoyed the dinner that your guide had arranged for. It is so rewarding to know that you all had a great time and felt right at home, we... More 

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