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Great Oak Manor

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290 Reviews from our TripAdvisor Community

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Showing 290: English reviews
Tall Timbers, Maryland
2 reviews
5 of 5 stars Reviewed 6 days ago NEW

Gorgeous Victorian B&B with its own private beach and access to the neighboring marina's beach and pool. Lots of lounge chairs and hammocks on the beach to enjoy the sunset. All the staff was very friendly and accommodating. They have a really nice spread for breakfast---homemade granola, usually bacon or sausage, something with eggs, and a variety of muffins and... More 

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

Thank you so much for your kind words. We take great pride in giving our guests top notch service and it's wonderful to know that it is appreciated. We are thrilled that you enjoyed your stay and do hope that you will come back again soon! Mike More 

Reisterstown, Maryland
Level Contributor
3 reviews
3 hotel reviews
INNKEEPER’S FAVORITE REVIEW
5 of 5 stars Reviewed 4 weeks ago

Between Vickie Cunningham and Innkeeper Mike Sorrels our stay was pure enjoyment, as a matter of fact we loved it so much we stayed an extra night!! Hospitality is amazing, attention to detail is exceptional. The staff is hardworking and attentive and the grounds are immaculate. From the moment we walked through the front door we felt completely welcome. If... More 

Helpful?
Thank Michelle Y
About Innkeeper's Favorite Review
The Innkeeper’s Favorite Review is a recent traveler review pinned as a favorite by this property’s owner or manager.
Las Vegas, Nevada
1 review
4 of 5 stars Reviewed 1 week ago

Unique setting thanks to Mother Nature and unique elegant property thanks to good taste and hard work! Best neighborhood for wonderful sunsets and a grand lawn to offer it justice and just relax taking in great view of the Bay!! Each room offers its own personality and our room helped us to relax and be brought to a different time!... More 

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

Thank you for reviewing our property, We sincerely apologize for not meeting the 5 star expectation! We strive for the very best in service. Please feel free to contact me directly with any insight on how we can make future stays better for your family and every family we serve. Thank you Mike Sorrells More 

Level Contributor
4 reviews
5 of 5 stars Reviewed 1 week ago

We enjoyed the manor and the beautiful surroundings, Mike was always great and helpful and met your every need.The breakfasts were delicious and plentiful, our room was spacious and comfortable and quiet.We couldn't havre asked for a better place to spend a relaxing weekend.We will tell all our friends this is the place to go in Chestertown , Md.We hope... More 

Helpful?
Thank Bernadine W
GOMStaff, Manager at Great Oak Manor, responded to this review

So glad you enjoyed the Manor! Its a very quiet and peaceful place to rest anytime of the year! Come see us again soon! Thanks Mike More 

Wilmington, Delaware
1 review
5 of 5 stars Reviewed 2 weeks ago

My husband and I just returned home from 2 days at Great Oak Manor. It's one of the loveliest B&B's I've ever stayed at. The property is just stunning, and the views of the Chesapeake Bay are amazing. I'm not sure where to start with my review, there are so many good things to say. The innkeepers are gracious and... More 

Helpful?
Thank LynnG113
GOMStaff, Manager at Great Oak Manor, responded to this review

Thank you Lynngallo, for the gracious review! We pride ourselves in being committed to our customers.. We look forward to your return. Until we meet again, The Staff of Great Oak Manor!.. More 

New York City, New York
1 review
5 of 5 stars Reviewed 3 weeks ago

I visited Great Oak Manor with my husband, young child, and dog in early July. The manor even more beautiful than the photographs online. With beautiful views of the bay, and bald eagles swooping overheard, rolling lawns, and hammocks for the guests, we couldn't have asked for a more magnificent and relaxing vacation. The innkeepers were warm, attentive, and thoughtful,... More 

Helpful?
Thank kattieJ578
GOMStaff, General Manager at Great Oak Manor, responded to this review

Thanks so much for taking the time to review our piece of paradise! So glad you and your family had a great time! We look forward to having you back very soon! Always keep an eye on the Specials and Packages section of our website! Take care and see you soon! More 

Cranston, Rhode Island
Level Contributor
12 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 7 helpful votes
5 of 5 stars Reviewed 3 weeks ago

From the moment we arrived we were greeted by Innkeepers Mike and Vickie and welcomed graciously and felt right at home in this Grand Manor. The manor was a beautiful Bed and Breakfast and Mike and Vickie were more than happy to help us with anything we needed. Driving up to the manor was like something out of the past... More 

Helpful?
Thank Michelle L
GOMStaff, Manager at Great Oak Manor, responded to this review

Thanks Michelle for such an amazing review, I'm glad we were able to make your stay more enjoyable and we look forward to seeing you again soon. Remember to always check our specials and promotions for your next stay! See you soon and take care! Michael & Vickie More 

Hagerstown, Maryland
Level Contributor
24 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 13 helpful votes
1 of 5 stars Reviewed 3 weeks ago

My Husband and I stayed at the Great Oak Manor over the weekend of June 24th-25th. We had a wonderful weekend......Innkeepers Scott and Kaylin Benfield were absolutely great. Our room (Marmaduke) was clean and adequately furnished. Scott and Kaylin helped us with our luggage..along with their helper. Wine and cheese were waiting for us as ordered. Throughout the weekend we... More 

Helpful?
2 Thank Bigeye149
Media, Pennsylvania
1 review
5 of 5 stars Reviewed June 25, 2016

Great Oak is a perfect place for a family reunion. Beautiful site and large lawn for all sorts of games. There are 12 guest rooms so can accommodate a large group. Gathering around the fire pit in the evening always enjoyed.

Review collected in partnership with this hotel

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

Hi Janet, We certainly enjoyed hosting yourself as well as your family for a reunion. We were so pleased that you all enjoyed the rooms, grounds and amenities. We do hope to see you all again next year! Kaylin Benfield, Innkeeper More 

Southampton, Pennsylvania
Level Contributor
7 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
4 of 5 stars Reviewed June 22, 2016

The views were great (Saw a beautiful bald eagle). The staff were extremely courteous and friendly. Our only disappointment was the condition of the carpeting in the bedroom. This is likely attributable to the fact it was a pet friendly room.

Review collected in partnership with this hotel

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

Hi Dennis, We are so pleased that you enjoyed your stay as well as were able to see one of the bald eagles that call our shoreline home. We are always working on room improvements and have plans to replace carpet in several areas, we appreciate your feedback! We do hope that you will join us again soon to enjoy... More 

Questions? Get answers from hotel staff and past guests. Ask a question

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Questions? Get answers from hotel staff and past guests. Ask a question

Amenities

Highlights
  • Free Parking
  • Free Breakfast
  • Beachfront
  • Bar/Lounge
  • Free High Speed Internet ( WiFi )
GreenLeadersGold level
About the property
  • Beachfront
  • Non-Smoking Hotel
  • Pets Allowed ( Dog / Pet Friendly )
Things to do
  • Bar/Lounge
Room types
  • Non-Smoking Rooms
  • Family Rooms
  • Suites
In your room
  • Air Conditioning
Internet
  • Free Internet
  • Free High Speed Internet ( WiFi )
Services
  • Free Parking
  • Free Breakfast
  • Meeting Rooms
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
Location: United States > Maryland > Chestertown
Price Range: $207 - $297 (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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