We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers: Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
The property is absolutely gorgeous, and the innkeepers, Holly and Richard, tended to every detail to make my stay as relaxing and restorative as possible! The common spaces are both gracious and welcoming, and the view of the bay is just stunning. I will be...More
Response from GREATOAKMANOR, Manager at Great Oak ManorResponded 6 days ago
Thank you Gini. We are so glad to here your stay was restorative for you. This is a special place and we love it when our guests realize it as well. We look forward to your next visit.
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
D'Oench Room was sop spacious and comfortable. Better yet was Holly, the innkeeper who had a million dollar personality. Her chickens provided fresh eggs produced one of my very best breakfasts. Holly also makes her own granola that was something extra special and a wonderful...More
Response from Holly M, Manager at Great Oak ManorResponded 1 week ago
Thank you for your kind comments. It is always a pleasure and very easy to be with such nice guests. We do indeed hope you will return at your earliest convenience.
We absolutely loved our stay at Great Oak Manor! The grounds were beautiful and the bay in walking distance; was great for fishing! The Carriage House was a wonderful accommodation, so comfortable and spacious! The breakfasts prepared were delicious, the peach homemade muffins were excellent! ...More
Response from Holly M, Manager at Great Oak ManorResponded 2 weeks ago
Thank you all for your wonderful review. We are so pleased to hear of your great experience. Our interim staff has a lot of experience and do a fantastic job so all guests will know no difference in our absence. We hope you will return...More
The setting, the staff, and of course the Manor are all great. If you need to get away from it all, come here. Both husbands and wives can be happy here. The Bay is beautiful, golfing and sailing close by, bikes provided, and plenty of...More
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travellers.
Free High Speed Internet ( WiFi )
US$167 - US$219 (Based on Average Rates for a Standard Room)
Star rating provided by Expedia.
Non-Smoking Rooms ,
Number of rooms
TripAdvisor is proud to partner with Booking.com, Expedia, Hotels.com, Cancelon, Orbitz, Travelocity, Hotwire and Priceline so you can book your Great Oak Manor reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday and business trips, always with the best discounts and special offers.
Response from Emmett4640 | Reviewed this property |
Scenery and wildlife at and near Great Oak is good but can't speak to what it's like in December. The Inn is five miles outside of town. Chestertown has nice shops and a great bookstore, but some stores and restaurants might... More
Scenery and wildlife at and near Great Oak is good but can't speak to what it's like in December. The Inn is five miles outside of town. Chestertown has nice shops and a great bookstore, but some stores and restaurants might close in December.
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
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 30. Please check our website.
Holly McKee, Manager/Innkeeper
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
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 :).
You may want to ask for a second floor room facing the beach, beautiful scenery. I was not on the third floor, but, I know three of the rooms had big fireplaces, walk in closets, big bathrooms on the second floor (one facing the front and two facing the back. This is just a wonderful old home that is in good condition. Their breakfasts were very good. Lots to eat. The employees are nice and will give you a tour of the house. Ask if they "forget" or are too busy. I can't say enough about this wonderful home. Our tour guides know the woman who lives and runs the home. The tour guides love to come here every year.
Are you sure you want to delete this answer?
"If you're going to Chesapeake Bay, pick a room with a view of the bay. It is to die for!"