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Traveller (181)
Room & Suite (50)
  • Excellent90%
  • Very good7%
  • Average1%
  • Poor1%
  • Terrible1%
Travellers talk about
“chesapeake bay”(76 reviews)
“music room”(14 reviews)
“private beach”(12 reviews)
Free Wifi
Free Parking
Breakfast included
Air Conditioning
Non-Smoking Hotel
3 Star Hotel
All hotel details
1 Apr2 Apr
1 room, 2 adults, 0 children
Standard Room
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Free Cancellation
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Reviews (387)
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All reviewschesapeake baymusic roomprivate beachview of the bayadirondack chairsb bbreathtaking viewsget awayeastern shorebald eaglescanada geesemy husband and ifire pitbreakfast was deliciousfrench toastback yardrock hall
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1 - 5 of 387 reviews
Reviewed 1 week ago via mobile

Great Oak Manor is a splendid B&B When entering the property, you will be impressed by the shear grandness of the Inn’s massive size. Once inside, the attention to architectural detail and tasteful decor is quite impressive. My husband, who is a builder of fine...More

Thank heathpaul
Response from General M, Manager at Great Oak ManorResponded 1 week ago

We so appreciate all of our guests and their kind remarks. I love the detail of this review as it speaks to everything about the Manor. Thank you for your kind words. We strive to make everyone's visit memorable and we look forward to having...More

Innkeeper's Favourite Review
Reviewed 30 May 2017

My husband and I had our 50th Wedding Anniversary planned for the week of May 20th in Newport. RI, where we met and were married. However, I had a stroke instead, so all of our plans had to be cancelled. Our friends had recently been...More

2  Thank rhodyred
Response from GREATOAKMANOR, Manager at Great Oak ManorResponded 8 June 2017

You know when we learned of your stroke and the cancellation of your plans, we knew we needed to make this a special time for the two of you. It is soooo easy to do that for kind and wonderful guests, such as yourself. You...More

Reviewed 8 February 2018 via mobile

I have been to Great Oak twice now-once by myself (with my dog!) and once with my partner (and my dog). Both times have been exquisite. The food is fantastic, the hospitality exceptional and it has a bit of everything. You can just relax on...More

Thank phillyqueenie
Response from General M, Manager at Great Oak ManorResponded 9 February 2018

Yes, we are Pet-Friendly. Our Lizzie loves having other dogs visit. We are so glad to hear you had a good experience with your furkid and hope all of you will return for another visit!

Reviewed 9 January 2018

We stayed at the Great Oak Manor for my son's wedding (at the Manor as well). We stayed in the Carriage House and it was great! Richard and Holly McKee were awesome! Anything we needed or questions they had were promptly taken care of for...More

Thank TJ E
Response from GREATOAKMANOR, Manager at Great Oak ManorResponded 10 January 2018

We appreciate all of our guests, but we especially appreciate your kind remarks during your visit. It was our pleasure having all of you here and we are so glad you enjoyed the wedding and your entire stay. I realize you live too far away...More

Reviewed 30 December 2017

A few girlfriends and I stayed in the Cottage while hunting Canada Geese for a few days. I must say I felt like I was spoiled!! The manor on it's own just has so much elegance and history to it, but the Cottage that was...More

Thank RachelleH164
Response from General M, Manager at Great Oak ManorResponded 31 December 2017

Now you all were a fun bunch of young women. It was our pleasure to meet you and we can't wait to see you again. Thank you for all the nice things you said and we are so glad you described your stay in the...More

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Awards & Recognition
GreenLeaders Gold level
Certificate of Excellence
Top amenities
Free Parking
Free High Speed Internet ( WiFi )
Breakfast included
Hotel Amenities
Free Parking
Breakfast included
Room amenities
Air Conditioning
Price range
US$163 - US$245 (Based on Average Rates for a Standard Room)
Hotel class
Room types
Suites, Non-Smoking Rooms, Family Rooms, Accessible rooms
Price range
US$163 - US$245 (Based on Average Rates for a Standard Room)
Hotel class
Room types
Suites, Non-Smoking Rooms, Family Rooms, Accessible rooms
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Traveller (181)
Room & Suite (50)
Pool & Beach (13)
Dining (3)
Business Centre & Event Rooms (6)
Family and Play Areas (3)
Questions & Answers
Ask a question
Christopher G
4 October 2017|
AnswerShow all 6 answers
Response from General M | Property representative |
Chestertown does not shut down nor do the restaurants. It is a vibrant town with lots to do and with a rich history of colonial times and fishing the Chesapeake. There are wineries near by and even a wine trail for... More
Laurie A
7 April 2017|
AnswerShow all 4 answers
Response from GREATOAKMANOR | Property representative |
Nightly rates vary as to the type of room and whether it is weekday or weekend day. This month April they range from $149-$349 for weekday nights and $189-399 for weekends. There are currently some specials until the April... More
21 October 2015|
AnswerShow all 2 answers
Response from mileyjackie | Reviewed this property |
Yes. I was with an all women's bicycle touring group in which some of the women were gay. They come back every year to this wonderful B&B. They are very nice. Both the employees of the establishment and the bicycle group... More
Room Tips
"If the Carriage House is available, I'd book it!"
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"If you want a bird's eye view of the magnificant sunsets, get a room on the back of the manor."
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"They are all great from what I can tell. We stayed in the 'D'Oench' room."
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"Get a bay view. Well worth it."
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