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“Hidden Gem on Chesapeake Bay” 5 of 5 stars
Review of Great Oak Manor

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Great Oak Manor
4.0 of 5 Inn   |   10568 Cliff Rd, Chestertown, MD 21620   |  
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Hotel website
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Hotel amenities
Special Offer
Midweek BOGO Special!
Ranked #3 of 11 Chestertown B&B and Inns
GreenLeadersBronze level
Doylestown, Pennsylvania
1 review
common_n_hotel_reviews_1bd8 2 helpful votes
“Hidden Gem on Chesapeake Bay”
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!!!!

  • Stayed June 2013, traveled with family
    • 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
Helpful?
2 Thank Roxylasalle
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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215 reviews from our community

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Westminster, Maryland
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 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++++++++!

  • 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
Helpful?
1 Thank Deborah739
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Level Contributor
5 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 3 helpful votes
4 of 5 stars 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
    • 4 of 5 stars
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    • 5 of 5 stars
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    • 5 of 5 stars
      Rooms
    • 4 of 5 stars
      Cleanliness
    • 5 of 5 stars
      Service
Helpful?
1 Thank Lenzai
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Greenwich, Connecticut
Level Contributor
36 reviews
12 hotel reviews
common_n_hotel_reviews_1bd8 22 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
Helpful?
3 Thank CJAP60
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Annapolis, Maryland
Level Contributor
39 reviews
14 hotel reviews
common_n_hotel_reviews_1bd8 27 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
Helpful?
Thank Charon2010
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Savannah, GA
Level Contributor
55 reviews
35 hotel reviews
common_n_hotel_reviews_1bd8 23 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
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    • 5 of 5 stars
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    • 4 of 5 stars
      Sleep Quality
    • 4 of 5 stars
      Rooms
    • 4 of 5 stars
      Cleanliness
    • 4 of 5 stars
      Service
Helpful?
1 Thank pollydick
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
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    • 5 of 5 stars
      Cleanliness
    • 5 of 5 stars
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Helpful?
Thank Michelle R
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
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 #3 of 11 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates):
Hotel Class:4 star — Great Oak Manor 4*
Number of rooms: 12
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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