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Great Oak Manor Inn

10568 Cliff Rd, Chestertown, MD 21620
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Hotel amenities
Great Oak Manor Inn
Ranked #4 of 12 Chestertown B&B and Inns
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131 reviews from our community

Traveler rating
    117
    8
    4
    1
    1
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Families
9
 
Couples
77
 
Solo
5
 
Business
4
 
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
Date Rating
Westminster, Maryland
2 reviews
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++++++++!

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Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
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... More

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Rye, New York
Contributor
16 reviews 16 reviews
6 hotel reviews
Reviews in 11 cities Reviews in 11 cities
8 helpful votes 8 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... More

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Annapolis, Maryland
Senior Reviewer
10 reviews 10 reviews
5 hotel reviews
Reviews in 8 cities Reviews in 8 cities
9 helpful votes 9 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... More

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Savannah, GA
Senior Contributor
32 reviews 32 reviews
25 hotel reviews
Reviews in 28 cities Reviews in 28 cities
10 helpful votes 10 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.

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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... More

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Philadelphia, Pennsylvania
Contributor
19 reviews 19 reviews
7 hotel reviews
Reviews in 9 cities Reviews in 9 cities
10 helpful votes 10 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... More

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New York City, New York
2 reviews
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... More

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Concord, Massachusetts
Senior Contributor
21 reviews 21 reviews
5 hotel reviews
Reviews in 7 cities Reviews in 7 cities
12 helpful votes 12 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... More

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Baltimore, Maryland
Reviewer
3 reviews 3 reviews
Reviews in 3 cities Reviews in 3 cities
3 helpful votes 3 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,... More

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Simply Bed and Bread
Great value on a similar hotel
Chestertown, MD
5 of 5 stars 101 Reviews
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Hotel Summarization (Beta)

What travelers say

  • Chesapeake Bay(13)
  • Fresh fruit(4)
  • Lounge chair(3)

Additional Information about Great Oak Manor Inn

Address: 10568 Cliff Rd, Chestertown, MD 21620
Phone Number:
Region: United States > Maryland > Chestertown
Amenities:
Bar/Lounge Beach Free Breakfast Free High-Speed Internet Free Parking Pets Allowed Suites Swimming Pool
Hotel Style:
Ranked #4 of 12 B&Bs / Inns in Chestertown
Price Range: $$
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
Great Oak Manor Hotel

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