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All 12 Chestertown B&Bs / inns

Great Oak Manor Inn

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10568 Cliff Rd, Chestertown, MD 21620
Hotel amenities
Great Oak Manor Inn
Ranked #6 of 12 Chestertown B&B and Inns
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147 reviews from our community

Traveler rating
    128
    12
    4
    1
    2
See reviews for
12
88
6
4
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
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There are newer reviews for Great Oak Manor Inn
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Glenn Dale, Maryland
1 review
5 of 5 stars Reviewed May 27, 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.

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Rising Sun, Maryland
1 review
4 of 5 stars Reviewed May 25, 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... More 

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Washington DC, District of Columbia
Reviewer
5 reviews 5 reviews
3 helpful votes 3 helpful votes
4 of 5 stars 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... More 

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Philadelphia, Pennsylvania
Top Contributor
51 reviews 51 reviews
14 hotel reviews
21 helpful votes 21 helpful votes
5 of 5 stars 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... More 

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Hemel Hempstead, England, United Kingdom
Reviewer
5 reviews 5 reviews
5 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars 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... More 

Was this review helpful? Yes 1
Doylestown, Pennsylvania
1 review
2 helpful votes 2 helpful votes
5 of 5 stars 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!!!!

Was this review helpful? Yes 2
Westminster, Maryland
Reviewer
3 reviews 3 reviews
2 helpful votes 2 helpful votes
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++++++++!

Was this review helpful? Yes 1
Reviewer
5 reviews 5 reviews
3 hotel reviews
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... More 

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Greenwich, Connecticut
Senior Contributor
35 reviews 35 reviews
12 hotel reviews
21 helpful votes 21 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 

Was this review helpful? Yes 3
Annapolis, Maryland
Senior Contributor
33 reviews 33 reviews
12 hotel reviews
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... More 

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Additional Information about Great Oak Manor Inn

Address: 10568 Cliff Rd, Chestertown, MD 21620
Location: United States > Maryland > Chestertown
Price Range (Based on Average Rates): $$
Number of rooms: 11
Also Known As:
Great Oak Manor Hotel Chestertown

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