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“A Local Treasure By Boat or Car” 5 of 5 stars
Review of Great Oak Manor Inn

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Great Oak Manor Inn
10568 Cliff Rd, Chestertown, MD 21620   |  
Hotel amenities
Ranked #5 of 12 Chestertown B&B and Inns
Annapolis, Maryland
Senior Contributor
32 reviews 32 reviews
11 hotel reviews
Reviews in 17 cities Reviews in 17 cities
24 helpful votes 24 helpful votes
“A Local Treasure By Boat or Car”
5 of 5 stars Reviewed September 4, 2012

My husband and I live in the Baltimore/Annapolis area and can't believe we have never discovered this wonderful place! We went by boat on Labor Day weekend and had no idea what to expect. Hundreds of boats were in the cove, tied up and enjoying the fun of Jellyfish Joels, the tiki bar on the beach. Band playing, drinks flowing and an enormous mix of people. Young, old, families, singles. Something for everyone at this place. Tiki bar, playgrounds, golf, boats, pool, tennis, nice restaurants with awesome staff!

We were lucky enough to land a boat slip on one of the piers even though we didn't have reservations. The staff were very accomodating and the yearly slip-holders that were around us could not have been more friendly. A HUGE shout out to Pier C for making us feel welcome. We used the pool, which has a nice outside bar area. We had dinner at the restaurant, Mangroves, which had a nice mix of local favorite dishes as well as the tried and true.

If you're a boater, the bath houses were very clean and convenient from any pier. They also have adapters for electric if you don't have the correct one needed for shore power. Water and cable are also included in the slip cost as well as all of the other amenities on the property. There are even golf carts that will pick you up and take you to and from the tiki bar beach. If you opt to tie up in the cove, there is a free water taxi (though tips are greatly appreciated) that will pick you up and take you to the tiki bar or restaurant.

A gem of a place and definitely a place we would go again by car or water.

  • Stayed September 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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139 people have reviewed this hotel

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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 (13)
Date | Rating
  • English first
  • Any
English first
Savannah, GA
Senior Contributor
40 reviews 40 reviews
29 hotel reviews
Reviews in 32 cities Reviews in 32 cities
20 helpful votes 20 helpful votes
4 of 5 stars Reviewed July 31, 2012

Great river views from room and expansive lawn in the back of a beautiful manor house. Spacious and comfortable room. Good staff...very accomodating. Ten minutes away from cute town with good restaurants. Would go back.

  • Stayed June 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
West Friendship, Maryland
2 reviews
5 of 5 stars Reviewed July 30, 2012

My husband and I stayed at the Inn for our 2 yr Anniversary. Jenn the Inn keeper made us feel right at home! When we got to our room we found a bottle of champagne with a little note telling us Happy Anniversary and enjoy our weekend. We took that bottle down to the water and enjoyed the views and sat on the beach area. It was like our private evening on the bay!The breakfast each morning was so good with all the homemade goodies! Our bed was so comfy neither of us wanted to get up but we were glad we did! Jenn helped us pick restaurants each night and her recommendations were perfect! We loved it so much we already booked another weekend to go back!

Room Tip: Highly recommend D'Oench
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  • Stayed July 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Philadelphia, Pennsylvania
Contributor
20 reviews 20 reviews
7 hotel reviews
Reviews in 9 cities Reviews in 9 cities
15 helpful votes 15 helpful votes
5 of 5 stars Reviewed July 30, 2012

From the moment we drove up to this beautiful manor we were impressed. The innkeeper, Jennifer, was gracious and welcoming. We had a romantic stay in the Marmaduke with the most incredibly comfortable bed I have ever slept on. [If I could have fit it into my suitcase I would have!] The next morning we were served a delicious french toast casserole that I am still craving. Long talks on the lawn facing the water with the soft sounds of breaking waves only added to our experience. And I did I mention the Tiki Bar at the marina was walkable from the grounds?!? No need to drive.
Synopsis: Breath-taking manor home. Slept like a dream. Ate like royalty. Returning soon.

Room Tip: Go for the Marmaduke if you want the best bed in history.
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  • Stayed July 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
New York City, New York
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
2 of 5 stars Reviewed July 29, 2012

We expected a clean B&B, but no. The main house is attractive, but the room assigned to us was incredibly dusty with icky carpet in the bathroom. We asked to be shown another room and ended up in a room with NO air conditioning and NO working television. All this for $200+ per night. We have stayed in the Brampton Inn in Chestertown, and the only reason we tried this inn instead was that the Brampton was sold out. Now we know why!

  • Stayed June 2012, traveled with family
    • 1 of 5 stars Value
    • 3 of 5 stars Location
    • 1 of 5 stars Sleep Quality
    • 2 of 5 stars Rooms
    • 1 of 5 stars Cleanliness
    • 3 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Concord, Massachusetts
Senior Contributor
21 reviews 21 reviews
5 hotel reviews
Reviews in 8 cities Reviews in 8 cities
11 helpful votes 11 helpful votes
4 of 5 stars Reviewed July 16, 2012

Spent 2 nights at the manor midweek. Gorgeous grounds, and view. Gracious staff. Amanda greeted us, Jennifer gave us great suggestions for things to do and places to eat. Loved the Blue Crab sunset Cruise in Rock Hall, and eating at the Kitchen there for lunch. Loved Mount Harmon Plantation, another suggestion. Generous breakfast with personalized service. Nice afternoon snacks as well. Impressive manor with a sweeping central staircase. Downstairs is very well cared for. Some updating needed in our room. Stayed in the RingGold. High ceiling, king size bed, and generally comfortable. The bathroom floor needs updating (Carpeting should be replaced by tile.) outdoor chairs On the lawn the chairs needed to be replaced, and were removed our second day, with new ones ordered. We were in the area for a wedding and would return again if vacationing near Chestertown. Great for peace and quiet and beauty.

  • Stayed July 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Baltimore, Maryland
Reviewer
5 reviews 5 reviews
Reviews in 5 cities Reviews in 5 cities
4 helpful votes 4 helpful votes
4 of 5 stars Reviewed July 9, 2012

We traveled to Great Oak for a 2-night getaway. We chose it for the location--on the Eastern Shore near Chestertown and Rock Hall, and because it is right on the water. The view is excellent,as we had hoped, and the overall setting is very nice. Beautiful grounds, peaceful setting. We had a very nice experience. We were greeted by Amanda, who gave us a great welcome and introduction to the Inn. The Inn was quiet and comfortable, with the amenities we like--dvds to borrow and watch in the room, good snacks in the afternoons and cold drinks available all the time. We also liked that there were beach towels and water shoes available, though we did not use them this trip. Breakfast was good enough, and pleasantly served. Our room was clean and comfortable, and large compared to other places I've stayed. We lucked out and got one of the new mattresses--GREAT investment--we slept very well. Next investment should be a new shower head. I agree with some of the other reviews that there are aspects of the decor that need to be updated, but that will not keep me away. I will come back to enjoy the peace and quiet, the beautiful view and grounds, a large, comfortable room, and the friendly but unobtrusive staff. As mentioned by others, upon the suggestion of the innkeeper we tried the blue crab charters sailing trip--this was a lot of fun and a good deal. Great suggestion.

  • Stayed July 2012, traveled as a couple
    • 3 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

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Additional Information about Great Oak Manor Inn

Address: 10568 Cliff Rd, Chestertown, MD 21620
Location: United States > Maryland > Chestertown
Amenities:
Bar / Lounge Beach Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Pets Allowed ( Dog / Pet Friendly ) Suites Swimming Pool
Hotel Style:
Ranked #5 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $$
Official Description (provided by the hotel):
Great Oak Manor on the eastern shore of the Chesapeake Bay is aglow in warm sunsets; where towering Oaks gently kiss the skyline; and where you can let your body rest and your mind wander. Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century country-style estate rests alongside the waterfront. With 11 guestrooms, Great Oak offers the finest in a romantic luxury bed and breakfast inn. ... more   less 
Also Known As:
Great Oak Manor Hotel Chestertown

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