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Great Oak Manor

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10568 Cliff Rd, Chestertown, MD 21620
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1 room 1 guest
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176 Reviews from our TripAdvisor Community

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Traveler rating
    155
    13
    5
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    2
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14
111
6
5
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    5 of 5 stars
  • Rooms
    4.5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
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Milford, Connecticut
1 review
5 of 5 stars Reviewed yesterday NEW

Very nice bed and breakfast. I would recommend it highly. Scott and Kaylin are very nice people, new to this particular B&B, but have been in the business for awhile. Scott was very helpful when my truck broke down he offered to give us a ride to a restaurant in town, and pick us up. That is really going out... More 

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Freehold, New Jersey
Level Contributor
6 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 2 days ago NEW

If you are looking for a luxurious and peaceful getaway, GOM is a perfect choice. As a frequent visitor of B&B 's through the years, I can honestly say that this Inn is like nothing else I have been to before (in this $$$ range). With the view of the Chesapeake Bay combined with the general sereneness of the area... More 

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Springfield, Virginia
1 review
5 of 5 stars Reviewed 1 week ago

We highly recommend The Great Oak Manor! The Manor itself is a stately and impressive brick, colonial-styled mansion constructed in the late 1930s. The mansion has a large brick addition, utilized as a conservatory and event situs, that was constructed a few years ago and is fully consistent with the architecture of the mansion. The grounds are rather extensive and... More 

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Wilmington, Delaware
1 review
5 of 5 stars Reviewed 2 weeks ago

Everything was great! The staff was very courteous and helpful. All food preparations were unique, well prepared and presented. Love the old charm and country feel. Wonderful weekend getaway, looking forward to our next stay during the week.

Was this review helpful? Yes
GOMStaff, Assistant Innkeeper at Great Oak Manor, responded to this review

Theo, It was a pleasure having you stay with us! Thank you for taking the time to share your review with us; it's always great to hear from our guests and get feedback. We hope to see you back soon! More 

mt airy
1 review
5 of 5 stars Reviewed 2 weeks ago

It was beautiful! Clean, beatific views, comfortable. The innkeepers couldn't have been nicer or more accommodating. We brought our bass boat and had the most relaxing time we've had in a long time. We will definitely go back!

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GOMStaff, Assistant Innkeeper at Great Oak Manor, responded to this review

Sharon, Thank you for taking the time to share your kind review with us. We are thrilled to hear your trip was enjoyable and relaxing! We hope to see you back soon! More 

Annapolis, Maryland
Level Contributor
14 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed 2 weeks ago

We stayed at the Great Oak Manor Inn for two fabulous nights, while visiting Chestertown and the Eastern Neck wildlife refuge. Our room was the D'Oench which overlooked the Chesapeake Bay and the beautiful backyard grounds of the manor house. Our bed was very comfortable, the linens were beautiful and soft, the room was spacious, perfectly appointed just like all... More 

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GOMStaff, Assistant Innkeeper at Great Oak Manor, responded to this review

Mindy, We are pleased to hear you had a lovely 2-night stay with us last week and it was a pleasure having you both here. The D'Oench is always a fantastic choice of room and we are glad the bed and linens added to your enjoyable experience. Thank you for taking the time to share your wonderful review. More 

Pennsylvania
Level Contributor
6 reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed 3 weeks ago

We were very impressed with our accomodations the pillowsmand linens were super comfortable always a thing with us the location is beautiful and the innkeepers were wonderful. Loved the tea time pound cake and port.

Was this review helpful? Yes
GOMStaff, Assistant Innkeeper at Great Oak Manor, responded to this review

Thank you for taking the time to review and we're glad to hear you enjoyed the linens (we use Comphy brand sheets and agree they're divine). We hope to see you back here in the future! More 

New York City, New York
1 review
5 of 5 stars Reviewed 3 weeks ago

We stopped overnight on our way to a wedding in North Carolina. Great Oak Manor was the perfect place to transition from the pressures of NYC to the stresses of a friend's wedding weekend. The location was serene and quiet during our mid-week stay. The staff was helpful and friendly from the moment they opened the door until they helped... More 

Was this review helpful? Yes
GOMStaff, Assistant Innkeeper at Great Oak Manor, responded to this review

Ron, I'm thrilled to hear that Great Oak Manor was able to serve as a stress-free stop in the midst of your travels. I'm also extremely happy to see you note the improvements we've been working towards since our new ownership. It's also a win when we keep the teens happy! We certainly hope you find those extra days to... More 

Franklin, Massachusetts
1 review
5 of 5 stars Reviewed 3 weeks ago

Great Oak Manor is a great getaway. The rural location is great and the sunsets on the bay are truly a sight to see each evening! The grounds and rooms are charming and can easily bring one back to a time when life was much less hectic. The new Innkeepers, Scott and Kaylin were wonderful. They have some great ideas... More 

Was this review helpful? Yes
GOMStaff, Assistant Innkeeper at Great Oak Manor, responded to this review

We certainly hope you make it for a return visit to see the progress of our new innkeepers! It was a pleasure to have you both here and we appreciate you taking the time to share a review. If anything, you must come back for our sunsets. Thank you! Amanda More 

Baltimore, Maryland
2 reviews
common_n_hotel_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed 4 weeks ago

Elegant, Relaxing, ... simply Wonderful. Honestly, I believe this is the most luxurious and beautiful B&B on the Chesapeake Bay - Period. The Manor, itself, and the surrounding property are breathtaking. They will delight and amaze you. The Manor has just received two new innkeepers - Kaylin and Scott Benfield. They welcomed us to this waterfront retreat and made us... More 

Was this review helpful? Yes 2
GOMStaff, Assistant Innkeeper at Great Oak Manor, responded to this review

Thank you so much for your glowing review Peri! We are thrilled to hear that you enjoyed your time with us and would love to have you back as a guest anytime! We're glad you manage to find our wonderful gem on the Chesapeake. -The Great Oak Staff More 

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