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Great Oak Manor

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325 Reviews from our TripAdvisor Community

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Showing 325: English reviews
Reviewed 5 days ago NEW

Had a wonderful weekend getaway at Great Oak Manor. Mike and Lynne were so welcoming and helpful. Mike recommended a local restaurant that was just great. Even called a made reservations for us. The room was very comfortable and a had a great view overlooking the Bay. Breakfasts were delicious and generous. The Inn has a lovely solarium, and period...

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Helpful?
Thank Bill C
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Thank you for taking the moment to review us! Your review is gracious and kind we truly feel like service is the most important part of a vacation. Barbara's on the bay is great spot it visit for anyone in the area. Thanks again and hope to see you soon. Mike

Sparks, Maryland
Reviewed 1 week ago

If you want to take a break from the mayhem of modern living, Great Oak Manor is a great diversion. The innkeepers Mike and Lynne are warm and inviting, while the beautiful historic home located on the waterfront of the Chester River reminds you your on a vacation to relax. The Manor's location is centrally located for exploring the Eastern...

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Helpful?
Thank elev88
GREATOAKMANOR, General Manager at Great Oak Manor, responded to this review

It was our pleasure to have you folks at the Manor. So glad you enjoyed our little section of the Eastern Shore. The beauty and traditions thrive around us. See you soon. Mike

Montclair, New Jersey
Reviewed 2 weeks ago

Charming. My wife and I with two Corgis had a fantastic 3 night stay at Great Oak Manor. We loved the water views and spacious accommodations. So relaxing. Michael and Lynn could not have been more welcoming. We are coming back!

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Thank 2travelman
Washington DC, District of Columbia
Reviewed 6 December 2016

There is no way to get off the 3rd floor if there is an emergency. Also the fire extinguisher in my room has not been inspected since 2007. Most of the lights were turned off when we came back from dinner so it made it hard to see. Also I was not able to find any staff later in the...

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Helpful?
Thank bobindc43
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Bobindc43, Thanks you for taking the time to review us here at Great Oak Manor. We feel very strongly about your review and are taking some steps to ensure safety as best we can. Perhaps we failed to tell you in our facility tour that we participate TripAdvisor Eco Friendly program were we take several steps to ensure we do...

Reisterstown, Maryland
Reviewed 27 November 2016

This is our second stay at Great Oak Manor but it felt like we were coming home. Mike, Lynne and Bill, thank you again for an amazing get-a-way! We enjoyed 3 nights in the D'Oench room (second floor). The views are stunning and the room spacious with a real fireplace. The bed is incredibly comfortable yet firm enough that you...

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2Thank Michelle Y
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Michelle and Melissa, Thank you for your wonderful review. It was a pleasure spending the holidays with the both of you! I'm glad you enjoyed your meals here with us. We very much enjoyed the addition of your sauerkraut suggestion to our Thanksgiving meal and it will be a must have next year! The Russell room will be a great...

Reviewed 27 November 2016 via mobile

We stayed in the Russell room Thanksgiving Day weekend and we couldn't have left more relaxed. The breakfast Mike provided was excellent the grounds were great the local restaurants were terrific especially the Bay Wolf the room was fantastic the history interesting the staff was courteous and professional

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2Thank rockborn s
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Thank you for the great review. We are so pleased that you had such a relaxing holiday weekend stay. We are glad to hear that you enjoyed the surrounding area and restaurants as well. Chestertown is definitely a lovely quaint town to explore! Thanks again, Mike & Lynne

Easton, Pennsylvania
Reviewed 20 November 2016

We had stayed at this property before and were looking forward to another wonderful stay. Unfortunately, our experience on this visit left a lot to be desired. The location is wonderful, but that is where it ended. The inside of the building needs quite a bit of renovation, from very worn rugs, to painting of moldings to wallpaper coming off...

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Helpful?
Thank RoHoehler
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Although we strive for excellence, we sometimes encounter things like a faulty furnace which causes us to fall short. We have since solved the heating issues. Please contact us at the Manor so we can arrange for you to have another stay with us. It is very important to us that you experience the Manor at it's best. Thank you...

Pikesville, Maryland
Reviewed 8 November 2016

Right on the water, large property, well kept. It's as good on the inside as it looks on the outside. Elegant and classy with the most excellent staff we have encountered. Breakfast was great, our evening dinner on Friday a very pleasant surprise. More to do just around the Manor than we had time for, very highly recommended!

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1Thank F21208
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

We are so happy to hear you enjoyed your stay so much, as well as your Friday night dinner. It was our pleasure to help your stay here to be enjoyable. Thanks for the great review, Mike & Lynne

Mohnton
Reviewed 27 October 2016

The property is excellently maintained and the grounds are beautiful. Bikes and kayaks are free to use. While the inn's furnishings are formal, the feel is more casual in the dining area with a beautiful sun room that looks out over the lawn and river. Mike is very accommodating and professional as the innkeeper and quickly takes care of requests....

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1Thank Bob W
GREATOAKMANOR, General Manager at Great Oak Manor, responded to this review

Thank you for taking the time to review our Manor. We are so pleased that you enjoyed the grounds with the beautiful views along with our amenities. We agree, the carriage house is spectacular and is a must see! We look forward to having you back. Thanks, Mike

Philadelphia
Reviewed 20 October 2016

Beautiful place. We loved having use of the kayaks for the whole afternoon our first day. They were very kind to let us use them a bit early and provided great advice as to where to find lunch and dinner in the off season. The grounds very beautiful and well kept. Breakfast was delicious, homemade. The afternoon snacks and port...

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1Thank marston258
GREATOAKMANOR, General Manager at Great Oak Manor, responded to this review

Thanks for staying with us and for your review. We are so glad that you enjoyed our manor, grounds and amenities. We couldn't agree more that an afternoon on the kayaks is a great start to a getaway. We are sorry for the inconvenience with the wifi, we have put a lot of thought into this are will continue to...

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Amenities

Highlights
  • Free Parking
  • Breakfast included
  • Beachfront
  • Free High Speed Internet ( WiFi )
GreenLeadersGold level
About the property
  • Beachfront
  • Pets Allowed ( Dog / Pet Friendly )
  • Non-Smoking Hotel
Room types
  • Suites
  • Non-Smoking Rooms
  • Family Rooms
In your room
  • Air Conditioning
Internet
  • Free Internet
  • Free High Speed Internet ( WiFi )
Services
  • Free Parking
  • Breakfast included
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 

Additional Information about Great Oak Manor

Address: 10568 Cliff Rd, Chestertown, MD 21620
Region: United States > Maryland > Chestertown
Price Range: $189 - $325 (Based on Average Rates for a Standard Room)
Hotel Class:3.5 star — Great Oak Manor 3.5*
Number of rooms: 12
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Also Known As:
Great Oak Manor Hotel Chestertown
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Questions & Answers

Here's what travellers have asked, with answers from Great Oak Manor staff and other travellers.
2 questions
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Columbia, Maryland
Ocean City, New Jersey

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Typical questions asked:
  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

See which rooms travellers prefer

“Wait to book because they will drop the rate or give you half off”
 of 5 bubbles bobindc43, 6 Dec 2016 | Read review
“Do not book a room on the third floor. Too far up and in need of updating.”
 of 5 bubbles RoHoehler, 20 Nov 2016 | Read review
“D'Oench is a large room with a good view but no balcony. Caulk has the same view, it's a little smaller but has a small balcony area.”
 of 5 bubbles BobW60, 27 Oct 2016 | Read review
“Russel room fantastic”
 of 5 bubbles chemistandnurse, 18 Oct 2016 | Read review
“Every room is beautiful”
 of 5 bubbles frequentflyer3343, 14 Sep 2016 | Read review
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