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I normally do not review hotels but,,, While we have revisited this property a few times, it remains very special to us all in our family for its unique presence over the Bay and it architecture and wonderful inn keepers Holy, Richard and Lyn. Our...More
Response from GREATOAKMANOR, Manager at Great Oak ManorResponded yesterday
Thank you so much for your kind words. We strive to make all of our guests feel special and want them to enjoy everything about this amazing property. We are definitely looking 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 June 7, 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
We highly recommend this B&B for a stay in the Chestertown area. We stayed at Great Oak Manor for three nights in June. We travel with a child who has a food allergy, and the owners were very accommodating of his situation, for which we...More
Response from Holly M, Manager at Great Oak ManorResponded 6 days ago
Thank you for your kind words of our Manor and our staff. We are very lucky to have such a beautiful to live and work. I am so glad you spoke up about the temperature of your room as we want all of our guests...More
What a wonderful place for our first visit to the Chesapeake Bay. The comfortable room, delicious breakfasts, and beautiful sunsets were most enjoyable. We liked shopping in quaint Chestertown. There was a farmer's market in the town square the Saturday morning we were there. We...More
Response from Holly M, Manager at Great Oak ManorResponded 1 week ago
We are so glad to hear you had such a wonderful visit on your first visit to Chesapeake country. Don't forget the way here as we want to see you again very soon. Thanks for the kind words.
The upside to Great Oak Manor being a 20 minute drive from Chestertown is that guest enjoy a large, beautiful property, including a tiny private beach, hammocks and magnificent sunsets. The inn is beautifully appointed. It feels like a chateau in the French countryside. Breakfast...More
Response from GREATOAKMANOR, Manager at Great Oak ManorResponded 2 weeks ago
So glad you enjoyed your stay and appreciated the beauty of this area. We are, indeed, fortunate to live here and love sharing it with our guests. We hope to see you again in the near future.
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.
Free High Speed Internet ( WiFi )
$263 - $328 (Based on Average Rates for a Standard Room)
Star rating provided by Expedia.
Non-Smoking Rooms ,
Number of rooms
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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.
Response from GREATOAKMANOR | Property representative |
Hi there! If you choose to stay with us at Great Oak Manor Inn, you'll get a full breakfast with fresh seasonal fruit, cereal, yogurt, homemade baked goods, breakfast meat, and a hot entrée (French toast, eggs to order... More
Hi there! If you choose to stay with us at Great Oak Manor Inn, you'll get a full breakfast with fresh seasonal fruit, cereal, yogurt, homemade baked goods, breakfast meat, and a hot entrée (French toast, eggs to order, quiches, egg strata, etc) each morning of your stay. In terms of lunch or dinner in the area, there are several great places in Chestertown and Rock Hall.
Chestertown: The Lemon Leaf Café (lunch/dinner), JR's Past-Time Pub (lunch/dinner), Blue Heron (dinner), Play It Again Sam's (lunch), and several more.
Rock Hall: The Kitchen (lunch/dinner), Inn at Osprey Point (dinner), Waterman's, and Harbor Shack.
I hope this was helpful!
Amanda, Assistant Innkeeper
Great Oak Manor