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Great Oak Manor

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Great Oak Manor
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330 Reviews from our TripAdvisor Community

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Showing 330: English reviews
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Reviewed 5 days ago NEWvia mobile

Incredible customer service and a hidden gem on the water. So gorgeous and relaxing. It was so nice to get away from the city and escape. Highly recommend! The Caulk room was incredible:) The decor was so nice and I felt right at home as if I was in my own house. I can't say enough good things about it.

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

"I felt right at home..." is what we strive for and hope all our guests feel. The little balcony off the Caulk room is a nice, private place to drink some wine and watch the sunset. I'll bet you did that! Thank you for the review and we hope to see you for your next escape from the city. Vincent

Pennsburg
Reviewed 1 week ago

We love the manor. It is elegant and refined with first class service. Everyone is friendly and trying to make your stay a wonderful experience. I recommend that you visit their website and view all the rooms. Keep in mind that this is not a modern hotel but an elegant manor. It is located right on the bay so you...

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

Thank you for your gracious response. We are glad you took the opportunity to explore all the rooms in the Manor. Our various common rooms give our guests the ability to escape, unwind and relax. If you had been here just a couple days later, you would have had the opportunity to truly enjoy all the outside getaways also. We...

Maryland
Reviewed 1 week ago

This was our second visit to The Great Oak Manor in Chestertown. We highly recommend this B&B to all couples. The magnificent accommodations and panoramic view could only be topped by the courteous service. It may be a bit out of the way, but it truly deserves our greatest praise. Both Lynn and Vincent provide a wonderful experience.

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

We are so glad you had a chance to visit us and enjoy your Valentine's Day and anniversary escape. Special times call for special places and we are happy to help our guests celebrate these occasions. Thank you for your wonderful response. We hope to see you again soon. Vincent

New Jersey
Reviewed 3 weeks ago

We have returned to Great Oak every year since our wonderful wedding, which was in no small part to the innkeeper, Jen, at that time. Great Oak has changed ownership and is now on the second innkeeper since our wedding. Our last visit was the most disappointing. We reserved a room on the third floor to purposely avoid noise from...

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2Thank Tim G
GREATOAKMANOR, Owner at Great Oak Manor, responded to this review

Tim, We do appreciate your sharing your latest experience at our property. As the new owner, each and every guest experience is important and your comments have been reviewed and discussed with our team. We hope that you will return one more time, perhaps to celebrate your anniversary with us! We have a new experienced management team arriving early in...

A TripAdvisor Member
1 review
Reviewed 3 weeks ago via mobile

We chose this location for our anniversery getaway and were pleased with the pleasant experience. Everything was clean and comfortable. We loved the Geddes Piper room and it's beautiful view. The staff was lovely and attentive but gave us plenty of space. Chestertown was a cute little town and an easy drive from Baltimore. We would love to return for...

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Thank A TripAdvisor Member
GREATOAKMANOR, Guest Relations Manager at Great Oak Manor, responded to this review

We are pleased you enjoyed your stay so much and look forward to your next visit, which we hope will be soon.

Reviewed 18 January 2017

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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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 14 January 2017

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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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 5 January 2017

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
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

So glad that you and your wife enjoyed our pet-friendly property. Hope you'll return again and please bring the Corgis!

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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1Thank 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 28 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...

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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: $232 - $383 (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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Questions? Get answers from Great Oak Manor staff and past guests.
Posting guidelines
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

“Most rooms face the water. Perhaps one or two do not.”
 of 5 bubbles surferboyMaryland, 14 Feb 2017 | Read review
“Best advise, go to another BnB in Chestertown”
 of 5 bubbles timg753, 29 Jan 2017 | Read review
“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
5 of 5