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“Slice of Heaven on Maryland's Eastern Shore” 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
Westminster, Maryland
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
“Slice of Heaven on Maryland's Eastern Shore”
5 of 5 stars 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
    • 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.
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139 people have reviewed this hotel

Traveler rating
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11
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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
Reviewer
5 reviews 5 reviews
3 hotel reviews
Reviews in 3 cities Reviews in 3 cities
3 helpful votes 3 helpful votes
4 of 5 stars Reviewed April 11, 2013

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
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Rooms
    • 4 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.
Greenwich, Connecticut
Senior Contributor
27 reviews 27 reviews
10 hotel reviews
Reviews in 16 cities Reviews in 16 cities
12 helpful votes 12 helpful votes
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.
Annapolis, Maryland
Senior Contributor
32 reviews 32 reviews
11 hotel reviews
Reviews in 16 cities Reviews in 16 cities
26 helpful votes 26 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
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
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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.

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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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