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Great Oak Manor

Certificate of Excellence
GreenLeadersGold level
04/06/2017 05/06/2017
1 room 2 adults 0 children
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345 Reviews from our TripAdvisor Community

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Showing 345: English reviews
Weehawken, New Jersey
Reviewed 9 February 2016 via mobile

We had such a great weekend! The views were beautiful, the rooms were clean, and the bed was very comfortable. The innkeepers, Scott & Kaylin, were very accommodating, which made our stay easy and relaxing. Breakfast on Saturday was delicious. Excited to go back.

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Helpful?
Thank kaitcurr27
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Kait, We are so appreciative of your kind words and pleased to know that you enjoyed your stay at the manor. It was such a pleasure to have you as a guest and we hpe to see you back at the Manor again soon! Kaylin Benfield Innkeeper

Elkridge, Maryland
Reviewed 8 February 2016

I had such a great experience at the Manor this weekend. The Innkeepers were very accommodating and were as nice as can be. The breakfast that they provided were so delicious. I wish I was able to stay another day just to have the breakfast. The room I stayed in was call The Hynson. It had high ceilings and a...

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Helpful?
Thank Sara D
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Sara, It was such a pleasure having you as a guest and we are thrilled to know that you enjoyed your time at the Manor as well as enjoyed the breakfast. Please be sure to come and visit us again soon! Kaylin Benfield Innkeeper

Columbia, Maryland
Reviewed 8 February 2016

We stayed for one night on New Years Eve for our anniversary. We stayed in Geddes-Piper, and I got the Romantic Package as an add-on. Scott and Kaylin, the innkeepers who live on the premises, were wonderful about working with me on the timing of everything. I was nervous about making sure that the sparkling wine and strawberries were there...

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Helpful?
Thank LKenney07
GOMStaff, General Manager at Great Oak Manor, responded to this review

We are so pleased to hear that you enjoyed your stay as well as the romantic package. Geddes-Piper is such a unique and special room, what perfect way to celebrate your anniversary. It was a pleasure to meet you both and we look forward to having you back to enjoy the property in the warmer weather! Kaylin Benfield Innkeeper

Reviewed 7 February 2016

This Was a beautiful bed and breakfast. The innkeepers were very friendly. The breakfast was good. The view was outstanding and my room was very nice. It was very homey and relaxing and there was so many things to do. It was so much fun, I will definitely go back. I enjoyed my stay and will recommend it to anyone...

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Helpful?
1Thank Angelina R
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Anelina, thank you so much for your kind words! We certainly enjoyed having you as a guest and are so glad to know that you felt at home. We hope to have you back again soon. Kaylin Benfield Innkeeper

Stevensville, Maryland
Reviewed 17 January 2016

We had our 4th Annual Half Way to Spring Fling this weekend and we had a wonderful time. The innkeepers were outstanding. We felt completely at home, the manor was spotless. Our room (The Caulk Room) was gorgeous, the bed was so comfortable with a beautiful view of the bay. So excited that they are making additions to the already...

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Thank MLebling
GOMStaff, General Manager at Great Oak Manor, responded to this review

Dan and Michele, thank you so much for your kind words. We truly enjoyed having yourselves as well as your entire group and guests of the Manor. It is lovely to know that you felt so at home and we look forward to having you back to stay as well as stopping in any time over the summer! Kaylin Benfield...

Pittsburgh, Pennsylvania
Reviewed 16 January 2016 via mobile

The GOM is a nice place but we got caught up in some convoluted pricing structure. I ended up paying over $200/night for myself solo. Going rate in the Chestertown area is less than $100. I am sure better place in summer as really no amenities in winter. Becomes a bed and shower which is available for much less at...

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Helpful?
Thank Douglas S
GOMStaff, General Manager at Great Oak Manor, responded to this review

Thank you for your review, we apologize for any confusion in our quoted rates. Kaylin Benfield Innkeeper

Lutz, FL
Reviewed 11 January 2016

What a beautiful and serene bed and breakfast. So regal feeling and yet so homey and relaxed. We had a wonderful time. everything was very clean and updated and beautifully decorated for the holidays, as well. Breakfast was delicious and very nicely presented. We will be back some day. Thank you!

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Helpful?
Thank Nightengale106
GOMStaff, General Manager at Great Oak Manor, responded to this review

Thank you so much for your kind words. We are so happy you were able to enjoy the holiday decorations and that you were pleased with breakfast. We hope to have you back again soon! Kaylin Benfield Innkeeper

Lancaster, Pennsylvania
Reviewed 8 January 2016 via mobile

The worst part of our stay involves an incident with our car. The parking area was dark and inadequate for the number of cars. We were forced to park in the grass in front of those concrete blocks you see in parking lots. However, what we did not know and could not see due to absolutely no lighting, was that...

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Helpful?
2Thank MHeras
GOMStaff, General Manager at Great Oak Manor, responded to this review

We’re sorry that your review is what’s finally allowing us to resolve the incident with your vehicle that occurred during your visit. As we discussed at the time of the incident our insurance companies need to work together to resolve the claim and they are now since you’ve submitted your claim. Since your visit, the concrete bars have been inspected,...

Maplewood, New Jersey
Reviewed 6 January 2016

I'm sorry we could stay only one night. From the moment the hospitable innkeepers greeted us to the beautiful view of the sunset to the fabulous breakfast--the best B&B breakfast I've ever had--all of our needs were met (and many were exceeded). Although we did not have a room with a water view, we were not disappointed; the grounds are...

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Helpful?
1Thank Megan H
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Megan, Thank you so much for your kind words, we truly appreciate it. We are so thrilled to know that you enjoyed your stay. Please do come back and visit us in the warm weather! Kaylin Benfield Innkeeper

Philadelphia, Pennsylvania
Reviewed 5 January 2016

We just spent New Years weekend at the Great Oak Manor. We had been looking to go somewhere away from the hustle and bustle of the city to relax and unwind. We thought the Eastern Shore was a good place to look. After doing our research, we found the Great Oak Manor. We were impressed by the website and decided...

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1Thank CallmeAL123

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04/06/2017 05/06/2017
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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 High Speed Internet ( WiFi )
  • Free Internet
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 21620-4115
Region: United States > Maryland > Chestertown
Price Range: £203 - £273 (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.
3 questions
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Columbia, Maryland
Ocean City, New Jersey
1 month ago

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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

“Ask for a bay view room”
dvail04011, 6 May 2017 | Read review
“They do have dog-friendly rooms available.”
cbeenjammin, 23 Apr 2017 | Read review
“the website does not do the rooms justice. All have a little different flair.”
  • caulk room
846CherylP, 15 Apr 2017 | Read review
“Geddes Piper is charming! But I'm sure they are all awesome!”
kristins786, 9 Apr 2017 | Read review
“Ask for a water view, although you probably will enjoy the grounds one way or the other.”
djk_9, 3 Apr 2017 | Read review
5 of 5
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Prices are for 1 room, 2 adults
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