We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Save
Traveller (183)
Room & Suite (64)
Storyboard
Overview
  • Excellent90%
  • Very good7%
  • Average1%
  • Poor1%
  • Terrible1%
Travellers talk about
“chesapeake bay”(77 reviews)
“music room”(14 reviews)
“view of the bay”(13 reviews)
AMENITIES
Free Wifi
Free Parking
Breakfast included
Air Conditioning
Beachfront
Non-Smoking Hotel
Suites
3 Star Hotel
All hotel details
Additional information
Offers from Great Oak Manor
Special Offer: Luxury Romance Package 🌹
Offers from Great Oak Manor
Special Offer: Luxury Romance Package 🌹
{"containerClass":null,"containerAttributes":null,"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","moduleList":["handlers"],"divClasses":"prw_rup prw_ibex_photo_carousel","js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"},"dust":{"nav_controls":"ibex_photo_carousel__nav_controls"}},"scriptFlags":null}
Reviews (397)
Filter reviews
397 results
Traveller rating
347
31
7
5
7
Traveller type
Time of year
LanguageEnglish
347
31
7
5
7
Show reviews that mention
All reviewschesapeake baymusic roomview of the bayprivate beachadirondack chairsbreathtaking viewsget awaybald eaglescanada geesesterling roomeastern shoremy husband and ifrench toastbreakfast was delicioussun roomrock hallwatching the sunset
FilterEnglish
Updating list...
1 - 5 of 397 reviews
Reviewed 2 days ago

My family enjoyed a second visit to the Great Oak Manor and we were thrilled with our rooms, scrumptious breakfast, and amazing grounds. Holly and Richard were so helpful and we were having so much fun that we decided at the last minute to add...More

Thank Maria G
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 4 days ago

My husband and I stayed at the Great Oak Manor for two nights recently along with our dog, Rosie. The property is beautiful, comfortable, well-appointed, and relaxing, and our dog-friendly accommodations were the icing on the cake. We were able to take Rosie straight outdoors...More

Thank Sally E
Response from General M, Manager at Great Oak ManorResponded 3 days ago

Thank you Sally for your kind words and we are so glad to hear you enjoyed your stay so much. We love when our guests use and enjoy the property and amenities so much. Glad you both were able to relax. We look forward to...More

Reviewed 1 week ago

We're from Richmond, and we met friends from Long Island at this inn that was a comparable distance from both couples. We were pleased with the rooms (across from each other on the third floor), the breakfasts (served buffet-style, tasty and filling), the complimentary afternoon...More

Thank Donna W
Response from General M, Manager at Great Oak ManorResponded 1 week ago

Thank you for you kind review. Guests that are from larger metro areas usually find solace and relaxation by being on the Bay. While we are 8 miles from town, it is a pleasant 15 minute drive to fun shopping, nice restaurants and sandwich shops....More

Reviewed 1 week ago via mobile

It’s a beautiful place and water view with lack of hospitality. It was the first hotel or b&b in our entire lives trips when the host rejected us at the door because of our slightly early arrival. It was hot (97 degree fahrenheit) outside and...More

1  Thank saharandwilliam
Response from General M, Manager at Great Oak ManorResponded 1 week ago

Please accept our apology for the most unfortunate stay of your B&B experience. Check in is clearly stated in our correspondence with you as 3pm. However, it is our policy to welcome all guests upon an early arrival by letting them know their room may...More

View more reviews
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 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
Hotel Amenities
HOTEL FEATURES
Free Parking
Free High Speed Internet (WiFi)
Breakfast included
Beachfront
Air Conditioning
Banquet Room
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
Hotel class
Contact Information
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
Add Photo Photos
Traveller (183)
Room & Suite (64)
Pool & Beach (14)
Dining (7)
Business Centre & Event Rooms (5)
Family and Play Areas (3)
Questions & Answers
Ask a question
Christopher G
5 October 2017|
AnswerShow all 6 answers
Response from General M | 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
"Roese Room is lovely and great for a family; Sterling Room is ground floor and is also good for a family."
Read review
"3rd floor rooms are smaller, more affordable, and generally have better views than the lower floors. Worth..."
Read review
"If the Carriage House is available, I'd book it!"
Read review
"If you want a bird's eye view of the magnificant sunsets, get a room on the back of the manor."
Read review
Is This Your TripAdvisor Listing?
Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more. Claim Your Listing