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“Fabulous and comfortable!” 5 of 5 stars
Review of Great Oak Manor Inn

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Great Oak Manor Inn
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10568 Cliff Rd, Chestertown, MD 21620   |  
Hotel amenities
Ranked #6 of 12 Chestertown B&B and Inns
Greenwich, Connecticut
Senior Contributor
31 reviews 31 reviews
11 hotel reviews
Reviews in 19 cities Reviews in 19 cities
21 helpful votes 21 helpful votes
“Fabulous and comfortable!”
5 of 5 stars Reviewed October 9, 2012

My wife and I are frequent inn lodgers yet Great Oak was especially impressive with a handsome exterior and exquisite interior replete with old-school architectural details.

The property is lovely and the breakfast was terrific! The manager took the trouble to introduce herself and the staff was very accomodating.

The whole inn reminded us of our favorite B&B on a grander scale: Sweetwater Farm in Glen Mills, PA.

We are looking forward to our next trip and I'm thinking of trailing my boat down there for some spring bass fishing (out of the marina next door).

Room Tip: the inn is on the western side of Maryland's "eastern shore" so rooms on the back of...
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  • Stayed September 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes 3
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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147 reviews from our community

Traveler rating
    128
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    4
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Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    4.5 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 (15)
Date | Rating
  • English first
  • Any
English first
Annapolis, Maryland
Senior Contributor
33 reviews 33 reviews
12 hotel reviews
Reviews in 17 cities Reviews in 17 cities
28 helpful votes 28 helpful votes
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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Savannah, GA
Senior Contributor
43 reviews 43 reviews
31 hotel reviews
Reviews in 34 cities Reviews in 34 cities
21 helpful votes 21 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
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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
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Philadelphia, Pennsylvania
Senior Contributor
23 reviews 23 reviews
7 hotel reviews
Reviews in 10 cities Reviews in 10 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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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.
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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 #6 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $$
Number of rooms: 11
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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