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Traveller (193)
Room & Suite (64)
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Overview
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10568 Cliff Rd, Chestertown, MD 21620-4115 See on map
AMENITIES
Free Wifi
Free Parking
Breakfast included
Air Conditioning
Beachfront
Non-Smoking Hotel
Suites
3.5 Star accommodation
Additional information
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Offers from Great Oak Manor
Offers & Announcements:🎉Midweek Special✨
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Rooms
25 Nov26 Nov
|
1 room, 2 adults, 0 children
Standard Room
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Reviews (420)
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420 results
Traveller rating
367
33
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LanguageEnglish
367
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All reviews chesapeake bay private beach view of the bay adirondack chairs breathtaking views get away my husband and i eastern shore drawing room sterling room bald eagles breakfast was delicious french toast rock hall watching the sunset beautiful property fresh fruit
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1 - 5 of 420 reviews
Reviewed 2 weeks ago via mobile

The Great Oak Manor is a beautiful estate. The landscape is beautiful, the views of the bay are incredible. Holly and Richard are super sweet and super helpful. We were away for a long weekend without kids and it was so nice. The fireplace in...More

Thank Annie M
Response from GeneralM223, Manager at Great Oak ManorResponded 2 weeks ago

Thank you for your wonderful review! We appreciate your assessment and are so glad you enjoyed your room and your fireplace. We are looking forward to your next visit when you need a break.

Innkeeper's Favourite Review
Reviewed 5 March 2018 via mobile

Great Oak Manor is a splendid B&B When entering the property, you will be impressed by the shear grandness of the Inn’s massive size. Once inside, the attention to architectural detail and tasteful decor is quite impressive. My husband, who is a builder of fine...More

Thank heathpaul
Response from General M, Manager at Great Oak ManorResponded 6 March 2018

We so appreciate all of our guests and their kind remarks. I love the detail of this review as it speaks to everything about the Manor. Thank you for your kind words. We strive to make everyone's visit memorable and we look forward to having...More

Reviewed 2 weeks ago

Great Oak Manor was the perfect place for a girls' get away. When I called to make a reservation, the person at the reception desk took a lot of time to help us choose the "best" rooms. The staff and Innkeepers Holly and Richard were...More

Thank lisa640
Response from GeneralM223, Manager at Great Oak ManorResponded 2 weeks ago

Thank you for your wonderful review. We are so pleased you enjoyed Great Oak Manor and your stay with us. We certainly enjoyed you both and look forward to your next visit.

Reviewed 3 weeks ago via mobile

This B&B is a select registry choice. I have stayed at their choices of B&B’s before. I must say the standard for this B&B are quit disappointing. My husband and I were celebrating our 23rd wedding anniversary. We were greeted and brought to the service...More

Thank francydecblu
Response from GeneralM223, Manager at Great Oak ManorResponded 3 weeks ago

My deepest apologies for your disappointing stay. The Manor house was built in 1938 as a private residence and the layout is exactly the same, as all who have owned it have striven to maintain the architectural integrity of the place. I am sorry you...More

Reviewed 3 weeks ago via mobile

We have just returned home from our stay at the Carriage House at Great Oak Manor. It was spot on wonderful and Holly could not have been more helpful and kind. There is no question that we will return again!

1  Thank sblitzerdr
Response from GeneralM223, Manager at Great Oak ManorResponded 3 weeks ago

Thank you for your kind words. We are glad you chose us as your place to stay for your son's wedding. We hope you will return when you can stay and relax-soon.

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About
Description
Great Oak Manor is situated on the Chesapeake Bay on Maryland’s Eastern Shore where the bay is aglow in vibrant, warm sunsets; where towering oaks gently kiss the skyline; and where you can let your body rest and More your mind wander. Tucked away on the outskirts of Chestertown, MD, our 12,000 square-foot Georgian-style estate has its own private beach. With 13 unique guestrooms, enjoy the finest in a romantic luxury bed and breakfast inn, where all of your whims are cared for. 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 on bike, kayaking on the bay, bird watching in our hammocks or just relaxing 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, & weddings. Welcome to our home, stay a while. Less
Hotel class
Contact Information
Hotel Amenities
HOTEL FEATURES
Free Parking
Free High Speed Internet (WiFi)
Breakfast included
Beachfront
Air Conditioning
Banquet Room
Electric Vehicle Charging Station
Laundry Service
Non-Smoking Hotel
Pets Allowed ( Dog / Pet Friendly )
Pool
Room Service
Restaurant
Bar/Lounge
Fitness Centre with Gym / Workout Room
Awards & Recognition
GreenLeaders Gold level
Certificate of Excellence
GreenLeaders Gold level
Certificate of Excellence
Room types
Suites, Non-Smoking Rooms, Family Rooms, Accessible rooms
Hotel class
Awards & Recognition
GreenLeaders Gold level
Certificate of Excellence
GreenLeaders Gold level
Certificate of Excellence
Contact Information
Room types
Suites, Non-Smoking Rooms, Family Rooms, Accessible rooms
Number of rooms
13
Price range
US$175 - US$250 (Based on Average Rates for a Standard Room)
Also Known As
Great Oak Manor Hotel Chestertown
Location
United States > Maryland > Chestertown
Hotel class
Awards & Recognition
GreenLeaders Gold level
Certificate of Excellence
GreenLeaders Gold level
Certificate of Excellence
Contact Information
Room types
Suites, Non-Smoking Rooms, Family Rooms, Accessible rooms
Number of rooms
13
Price range
US$175 - US$250 (Based on Average Rates for a Standard Room)
Also Known As
Great Oak Manor Hotel Chestertown
Location
United States > Maryland > Chestertown
Photos
Traveller (193)
Room & Suite (64)
Pool & Beach (14)
Dining (7)
Business Centre & Event Rooms (5)
Family and Play Areas (3)
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Questions & Answers
Ask a question
cdgrimes74
5 October 2017|
AnswerShow all 6 answers
Response from GeneralM223 | Property representative |
Chestertown does not shut down nor do the restaurants. It is a vibrant town with lots to do and with a rich history of colonial times and fishing the Chesapeake. There are wineries near by and even a wine trail for... More
0
Votes
Laurie A
7 April 2017|
AnswerShow all 4 answers
Response from GREATOAKMANOR | Property representative |
Nightly rates vary as to the type of room and whether it is weekday or weekend day. This month April they range from $149-$349 for weekday nights and $189-399 for weekends. There are currently some specials until the April... More
0
Votes
LKenney07
21 October 2015|
AnswerShow all 2 answers
Response from mileyjackie | Reviewed this property |
Yes. I was with an all women's bicycle touring group in which some of the women were gay. They come back every year to this wonderful B&B. They are very nice. Both the employees of the establishment and the bicycle group... More
1
Vote
Room Tips
"Choose a room with a view of the bay."
V9403ILjohnk
4 weeks ago
Read review
"Marmaduke is spacious and light. Spectacular view of Bay. Comfortable chairs, huge bathroom, walk-in..."
PMAMiddletown_DE
16 Sep 2018
Read review
"Rooms on the second floor west face the bay. A very good choice."
kimn44
17 Aug 2018
Read review
"The Tylden has a view of the bay with a small balcony."
cindye743
7 Aug 2018
Read review
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