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“Elegance in the countryside”
5 of 5 bubbles Review of Great Oak Manor

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Great Oak Manor
Ranked #2 of 11 Chestertown B&B and Inns
Certificate of Excellence
GreenLeadersGold level
Maryland
Level Contributor
100 reviews
11 hotel reviews
common_n_hotel_reviews_1bd8 53 helpful votes
“Elegance in the countryside”
Reviewed 16 June 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 4-5 miles outside of Chestertown proper, right on the shores of the bay. Driving up to it on the country (dirt) road, the "manor" in the name becomes obvious. With a packed, small-stone circular driveway in the front, the building could be the setting for a story from the early 20th century that we often see on PBS. There have been additions to the building to reach the total of 14 private rooms, but they are on the right side (behind a wall around the courtyard) and not in the main view of the manor.
While we were there for three days, to our disappointment, it rained for the first two. That did not prevent us from seeing the huge lawn overlooking the bay. There are numerous lawn chairs placed closer to the water where good weather would be a magnet for plopping down, camera at the ready, to watch what we heard are some of the most gorgeous sunsets anywhere. On our final day there, the weather was good enough for us to get a closer look at that area and to get closer to the water.
The innkeeper and her daughter were as nice as could be. The daughter took us on an inside tour of the manor as soon as we arrived. The innkeeper herself was a model of efficiency and friendliness, and seemed to be everywhere (but unobtrusively so) at the same time. As for the breakfasts, they were outstanding and creative. They will leave you finding it very easy to skip lunch and spend the day visiting many historic spots in the area, and then have a later dinner at one of the numerous restaurants in nearby Chestertown and Rock Hall.
We will look forward to returning for another visit when the weather is more accommodating.

Room Tip: Ask for a room with a view of the water. It's also better to get a room on the 2nd floor rather...
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  • Stayed June 2014, travelled as a couple
    • Value
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Helpful?
Thank billybosso
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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341 reviews from our community

Traveller rating
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56
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Rating summary
  • Location
    5 of 5 bubbles
  • Sleep Quality
    5 of 5 bubbles
  • Rooms
    4.5 of 5 bubbles
  • Service
    5 of 5 bubbles
  • Value
    4.5 of 5 bubbles
  • Cleanliness
    5 of 5 bubbles
Traveller tips help you choose the right room.   Room tips (72)
Date | Rating
  • English first
  • Any
English first
Glenn Dale, Maryland
1 review
Reviewed 27 May 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.

Room Tip: Room with a view of the water adds to your visit.
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  • Stayed December 2013, travelled as a couple
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Helpful?
Thank RMELTC
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Rising Sun, Maryland
1 review
Reviewed 25 May 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 a door that leads to a small porch area with a dirty table and two deck chairs...for the money select another room. We never met the Innkeeper which was disappointing. The breakfast was ok but I thing cherrios and yoplait yogurt really do not belong on the table of a inn such as this. The sherry and port were a nIce touch. The marina next door though really did not help the ambiance...at least on memorial day weekend. Bad garage band music really did not help the experience. Maybe that was just a holiday weekend deal but if that is a turnoff you better check with the marina to get the summer band schedule.Dont get me wrong...we enjoyed our stay. The inn is a bit dated but thats part of the charm. If you want all updated and new a 1938 bed and breakfast is not the way to go. The history of Chestertown and the old beach resorts of Kent County I find fascinating. Chestertown once being the busiest colonial port is a fact many do not realize. Its a nice weekend getaway for history buffs with enough dining and shopping to satisfy those not so locked to history. The tea party is fun even if not proven to be historically accurate...take a walking tour and learn all about that and some very interesting historical facts of the period....we paid 8 dollars for the tour and our guide was very interesting and informative.

  • Stayed May 2014, travelled as a couple
    • Value
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Helpful?
Thank traveler594652
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Washington DC, District of Columbia
Level Contributor
5 reviews
common_n_hotel_reviews_1bd8 3 helpful votes
Reviewed 15 November 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 well! Jennifer the innkeeper was a great host, a wonderful cook and an informative guide to the town and the area. She sent us to JR's bar for cream of crab soup and crab cakes, and we will be forever grateful.
On the less happy side, the building is looking a little tired, and some of the amenities were not up to par. The tub and shower in our room were old and past prime. A chair was stained and badly worn. The storm window was broken. Some decorating looked outdated as well, especially where they used plastic plants. We ranked the value as just average because of these issues.

Room Tip: We would recommend the D'Oench for the view and the comfortable bed, but the bath is old.
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  • Stayed November 2013, travelled as a couple
    • Value
    • Location
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Helpful?
Thank jackdonna46
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Philadelphia, Pennsylvania
Level Contributor
54 reviews
15 hotel reviews
common_n_hotel_reviews_1bd8 29 helpful votes
Reviewed 30 August 2013

Ok, not really, but seeing 4 bald eagles on the estate at Great Oak Manor was just as exciting for us! My husband chose this spot for us, needing a getaway. Long ago, he yacht sat for some older friends at the marina there and would go up to the Manor's hammocks to read and relax on land. They were very gracious letting him lounge there during the week when there were few visitors. He never went in the house.

It is a stunning example of Georgian architecture! The service is wonderful, friendly and prompt. I will warn you though, that the pillows are rock-hard -- but Lisa did scavenge 2 fluffy ones for me so my 2nd night's sleep was divine. The breakfast is wonderful.

The 'lap poop' wasn't working which was ok -- it's one of those high powered small 'pools' where you swim against the current. Would be great if they replaced it with a large jacuzzi.

Exploring Chestertown was soooo much fun! There is something for all adults! In the Manor, we met a couple from North Jersey who were leaving a day early because 'there's not much to do around here!' First of all, who cares! The Manor is on stunning grounds, has a private beach and also beach/pool/golf/tennis access at the Marina which is next door, and exploring Kent County could have kept us engaged for several weeks!

History, great food, just enough nice boutiques. Try the crab soup at the Lemon Leaf cafe, shop at Mimi's boutique and the uber cute Twigs and Tea Cups. All the shop proprietress were so friendly and welcoming.

Do drive down to Great Neck Federal wildlife preserve, Rock Hall, and explore, explore, explore.

Room Tip: Ask for a water view. Do be aware that there are rooms on the 3rd floor so if you have trouble with...
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  • Stayed August 2013, travelled as a couple
    • Value
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Helpful?
Thank VLD_60
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Hemel Hempstead, England, United Kingdom
Level Contributor
25 reviews
12 hotel reviews
common_n_hotel_reviews_1bd8 12 helpful votes
Reviewed 24 July 2013

After driving for 6 hours from NYC and arriving late at night we were greeted by a very friendly lady. We were meant to stay in a different suite but they were having troubles with the shower so she gave us a free upgrade. The manor was stunning and peaceful she gave us a small tour and told us we could come down a bit later for breakfast as we had had a long journey. When entering the suite we couldn't believe our luck it was like we were in our own house it was huge! My mum and sister had the master bedroom which they both said was the most indulgent sleep they have ever had! I slept in the other room which was just as comfy. The bathroom was huge, lots of towels and very clean. The next morning we came down for breakfast which was beautifully served and the inn keeper was exceptional in making our stay memorable. It was so good we booked another night! Would definitely recommend this Inn to anyone visiting Chestertown.

  • Stayed July 2013, travelled with family
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Helpful?
1 Thank Chanelle M
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Doylestown, Pennsylvania
1 review
common_n_hotel_reviews_1bd8 2 helpful votes
Reviewed 8 July 2013

We had a large family gathering for a 4 day weekend...The Inn is Gorgeous! The Food was Fantastic! The Staff is WONDERFUL!!!
Jennifer the Inn Keeper is so accomodating and the rest of the crew made us feel like we were at home!!
We can't wait to go again!!!!

  • Stayed June 2013, travelled with family
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Helpful?
2 Thank Roxylasalle
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

Property: Great Oak Manor
Address: 10568 Cliff Rd, Chestertown, MD 21620
Phone Number:
Region: United States > Maryland > Chestertown
Amenities:
Bar / Lounge Beach Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Pets Allowed ( Dog / Pet Friendly ) Suites
Hotel Style:
Ranked #2 of 11 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): ££
Hotel Class:3.5 star — Great Oak Manor 3.5*
Number of rooms: 12
Official Description (provided by the hotel):
Great Oak Manor is located on Maryland's Eastern Shore, where the Chesapeake Bay is aglow in vibrant, 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 Chesapeake Bay waterfront. With 12 guestrooms and various common rooms, Great Oak Manor offers the finest in a romantic luxury bed and breakfast inn, where all of your whims are cared for, day and night. Whether you're adventurous, need to get away, or just want to be taken care of, there's something here for everyone. Spend an afternoon perusing the quaint streets of historic Chestertown, exploring the Eastern Neck Refuge, sampling the fresh catch in Rock Hall, or just curl up in the arms of a weathered Adirondack chair to soak up the view. Aside from offering a relaxing getaway for travelers, Great Oak Manor also serves as the ideal location for various events, retreats, parties, and weddings. Welcome to our home, stay a while. ... more   less 
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Also Known As:
Great Oak Manor Hotel Chestertown

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