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.
All 12 Chestertown B&Bs / inns

Great Oak Manor Inn

Save Saved
You added Great Oak Manor Inn to your Saves list
10568 Cliff Rd, Chestertown, MD 21620
Hotel amenities
Great Oak Manor Inn
Ranked #5 of 12 Chestertown B&B and Inns
We can't find prices for this accommodation
Our online travel partners don't provide prices for this accommodation, but we can search other options in Chestertown
Check In Check Out
Write a Review

144 reviews from our community

Traveler rating
    127
    11
    4
    1
    1
See reviews for
11
86
6
4
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (14)
Date | Rating
  • English first
  • Any
English first
  • All months
    (144)
  • Mar-May only
    (41)
  • Jun-Aug only
    (46)
  • Sep-Nov only
    (34)
  • Dec-Feb only
    (23)
All months
Minneapolis
Top Contributor
96 reviews 96 reviews
93 hotel reviews
124 helpful votes 124 helpful votes
5 of 5 stars Reviewed 1 week ago

Stayed at the Great Oak for 3 nights on Womantours Maryland Eastern Shore bike trip. Loved it. Innkeeper Jenn was very welcoming, the accommodations were superb and the breakfasts were spectacular (so glad I was biking every day so I could enjoy the food to the max). Stayed in the 'Caulk' room. 2 single beds that appeared smaller then a... More

Was this review helpful? Yes
philadelphia
Senior Reviewer
6 reviews 6 reviews
4 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed 3 weeks ago

Spent 4 days and 3 nights at this lovely inn and thoroughly enjoyed our visit. The quaint town, Chestertown, was the location for many of our activities but we were able to visit other communities and see quite a bit of history of the region. Returning to the inn in between and preparing for dinner was the special treat. Breakfast... More

Was this review helpful? Yes
New York City, New York
Reviewer
4 reviews 4 reviews
4 hotel reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 20, 2014

My husband and I escaped to Great Oak Manor for a quick three day mini-moon after our wedding. Everything about our stay was perfect! The manor is beautiful, the food is delicious and the hospitality is exceptional! It was the perfect spot to sleep late, read on the grounds all day (and spot bald eagles in the trees just over... More

Was this review helpful? Yes
Baltimore, Maryland
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 7, 2014

I had heard about Great Oak Manor for years, but only recently had the opportunity to plan a trip myself. It was a little difficult to find(could use better signage) but it was well worth the backtracking. The manor itself is a gorgeous movie set like building, and the interior is decorated in an elegant,if faded charming way. However, the... More

Was this review helpful? Yes 1
McLean, VA
Contributor
11 reviews 11 reviews
7 hotel reviews
11 helpful votes 11 helpful votes
4 of 5 stars Reviewed July 23, 2014

We have returned to Great Oak Manor again and again. It's peaceful, quiet and uplifting. Rooms are well decorated and comfortable. The grounds are fantastic. There's not tons to do in the area so bring your bikes and fishing poles but mostly get ready to relax.

Was this review helpful? Yes 1
Sparks, Maryland
Reviewer
5 reviews 5 reviews
5 hotel reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed June 20, 2014

My wife and I spend a lot of our leisure time at B&B's and Inns, especially the Select Registry ones, and we both just loved this place ---- right on the water, beautiful grounds, fabulous common rooms, bald eagles and ospreys all about; just wonderful. The innkeeper, Jen, was just delightful; very warm and engaging, but always with an eye... More

Was this review helpful? Yes
Maryland
Top Contributor
77 reviews 77 reviews
7 hotel reviews
39 helpful votes 39 helpful votes
5 of 5 stars Reviewed June 16, 2014

We had lived in Maryland for a long time but had never been to Chestertown, just on the other side of the Chesapeake Bay and north from the Bay Bridge. Our children gave us a gift certificate to Great Oak Manor Inn for our anniversary last year, and we finally got a chance to use it. Great Oak Manor is... More

Was this review helpful? Yes
Glenn Dale, Maryland
1 review
5 of 5 stars Reviewed May 27, 2014

My wife and I celebrated coming her coming home from Iraq at Great Oak. Immediately, we decided we wanted to have our wedding here. Even 4.5 years later, we are still amazed with the location. Thanks.

Was this review helpful? Yes
Rising Sun, Maryland
1 review
4 of 5 stars Reviewed May 25, 2014

We celebrated a birthday and tea party weekend at the manor. It is a very impressive architectural example in beautiful surroundings with a wonderful view of the bay. We stayed in the Caulk room which was fine but I was mislead by the website describing a private terrace on which you can enjoy a sunset cocktail. It is more of... More

Was this review helpful? Yes
Washington DC, District of Columbia
Reviewer
5 reviews 5 reviews
3 helpful votes 3 helpful votes
4 of 5 stars Reviewed November 15, 2013

We had three wonderful days at the inn. The room had a beautiful view of the Bay and the grounds were gorgeous and great for walking. On the day we left, we saw a pair of bald eagles. We stayed in the D'Oench room, and had a great bed. It felt too soft at first touch but we slept very... More

Was this review helpful? Yes
Questions? Get answers from hotel staff and past guests. Ask a question
Do you own or manage Great Oak Manor Inn?
Register now for free — and start getting automatic notification of new reviews, responding to traveler feedback, adding new photos to your listing and much more.
Manage your listing

Been to Great Oak Manor Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Great Oak Manor Inn

Address: 10568 Cliff Rd, Chestertown, MD 21620
Location: United States > Maryland > Chestertown
Price Range (Based on Average Rates): $$
Number of rooms: 11
Also Known As:
Great Oak Manor Hotel Chestertown

63 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All traveler photos (62)
Viewed
Pool/beach area (4)
Viewed
View from room (11)
Viewed
Hotel & grounds (4)
Viewed
Room/suite (4)
Viewed
Business center/function rooms (1)
Viewed
Other (38)

Management photos: Courtesy of the property manager

Viewed
All management photos (2)
Viewed
View from room (1)
Viewed
Pool/beach area (1)
Hotels you might also like...
Check In Check Out
Price Your Stay