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“Beautiful inn and grounds”
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
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 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 Some decorating looked outdated as well, especially where they used plastic plants.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, traveled as a couple
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Thank jackdonna46
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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245 - 251 of 379 reviews

Reviewed August 30, 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, traveled as a couple
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Thank VLD_60
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed July 24, 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, traveled with family
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1  Thank Chanelle M
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed July 8, 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, traveled with family
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2  Thank Roxylasalle
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed April 20, 2013

I've been visiting Great Oak Manor since mid-1990's. Just returned from 4-day stay. As usual, it was difficult to leave the manor and everything it offers. If you're seeking a gorgeous view of the Bay, along with some peace, tranquility and exceptional comfort, this is the place for you. Great Oak is a true gem of Maryland's Eastern Shore. A++++++++!

  • Stayed: April 2013, traveled solo
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1  Thank Deborah739
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed April 11, 2013 via mobile

We stayed at the Great Oak Manor over a weekend to celebrate our wedding anniversary. It's gloriously situated right on the bay with a breathtaking sunset view which can be enjoyed from the glassed in conservatory on a chilly night or sitting in several romantically positioned adirondack chairs on the lawn. The manor is well decorated in the Georgian revival style as are the rooms. Guests are welcome to use the fireplaces in the common areas with the logs provided and some rooms also have fireplaces. We had two breakfasts and the first was to order as there were few other guests but the second day a lovely self serve buffet was laid out and the innkeeper was observant enough to provide us with a separate order of turkey bacon as we could not partake of the sausages. Overall our experience at this inn is was lovely. The bathroom in our room can probably use some updates but everything worked and the water pressure was good. The grounds are very well maintained and make for a good stroll if the weather cooperates. We'd love to come back here again.

  • Stayed: March 2013
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1  Thank Lenzai
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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
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3  Thank CJAP60
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

Address: 10568 Cliff Rd, Chestertown, MD 21620-4115
Phone Number:
Location: 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: $164 - $201 (Based on Average Rates for a Standard Room)
Hotel Class:3.5 star — Great Oak Manor 3.5*
Number of rooms: 13
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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