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All 12 Chestertown B&Bs / inns

Great Oak Manor Inn

10568 Cliff Rd, Chestertown, MD 21620
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  • Reviews (139)
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Great Oak Manor Inn
Ranked #5 of 12 Chestertown B&B and Inns
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139 people have reviewed this hotel

Traveler rating
    123
    10
    4
    1
    1
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11
83
5
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
Traveler tips help you choose the right room.   Room tips (13)
Date | Rating
  • English first
  • Any
English first
Sparks, Maryland
Reviewer
5 reviews 5 reviews
5 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed 3 weeks ago

My wife and I spend a lot of our leisure time at B&B's and Inns, especially the Select Registry ones, and we both just loved this place ---- right on the water, beautiful grounds, fabulous common rooms, bald eagles and ospreys all about; just wonderful. The innkeeper, Jen, was just delightful; very warm and engaging, but always with an eye... More

Was this review helpful? Yes
Maryland
Top Contributor
75 reviews 75 reviews
7 hotel reviews
37 helpful votes 37 helpful votes
5 of 5 stars Reviewed 3 weeks ago

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... More

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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
3 reviews 3 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
Senior Contributor
47 reviews 47 reviews
11 hotel reviews
20 helpful votes 20 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
4 reviews 4 reviews
4 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

Was this review helpful? Yes 1
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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): $$
Also Known As:
Great Oak Manor Hotel Chestertown

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Amenities

Bar / Lounge Beach Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Pets Allowed ( Dog / Pet Friendly ) Suites Swimming Pool
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 
Number of rooms
11

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