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Traveller (186)
Room & Suite (64)
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Overview
Hotel website
E-mail hotel
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
Visit Hotel Website
Offers from Great Oak Manor
Special Offer: 🍂Fall Midweek Special
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Reviews (410)
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410 results
Traveller rating
358
33
7
5
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Time of year
LanguageEnglish
358
33
7
5
7
Show reviews that mention
All reviewschesapeake bayprivate beachview of the bayadirondack chairsbreathtaking viewsget awayeastern shoresterling roombald eaglesmy husband and ibreakfast was deliciousrock hallfrench toastwatching the sunsetmade us feelbeautiful propertybed and breakfast
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1 - 5 of 410 reviews
Reviewed 2 days ago via mobile

Amazing scenery all the way around this peaceful place! The quiet little beach was our favorite place to relax at throughout our stay, it’s private so we didn’t have to worry about any strange visitors or any loud crazy kids running around. Our stay involved...More

Thank STEstates
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 1 week ago

This beautiful inn is all you could hope for — and more. The inn is magnificent and the view breathtaking. My husband and I recently spent 4 nights at Great Oak in celebration of our 20th anniversary. The Marmaduke Room — second floor corner room—was...More

Thank PMAMiddletown_DE
Response from GeneralM223, Manager at Great Oak ManorResponded 6 days ago

Thank you very much for your wonderful review. It is beautifully written and you captured the essence of the Manor perfectly. We are looking forward to your next visit which we hope will be sooner than later. Lizzie sends her regards too.

Reviewed 1 week ago via mobile

Charming atmosphere! The mansion was spectacular beautiful scenery in and out! Our suite had Comfortable pillows which is a big plus for the wife, very peaceful throughout our stay, no loud(rude) guests or staff. Very much enjoyed the Bay view from the dining room where...More

Thank WaterLife1967
Response from GeneralM223, Manager at Great Oak ManorResponded 6 days ago

Thank you for your review. I especially appreciate your kind words about Meranda who is new. She is a kind young lady and eager to learn. We look forward to your return.

Reviewed 2 weeks ago

The manor is most impressive and is located in a beautiful setting, overlooking the Chesapeake, and surrounded by farm fields. It is a quiet, serene spot. Breakfasts were excellent. Our room was spacious and comfortable. Holly, our hostess, could not have been more gracious. We...More

Thank Rita C
Response from General M, Manager at Great Oak ManorResponded 2 weeks ago

Thank you Rita for your gracious review of your stay. We love your description of the area as it is so perfect. We do hope you both will come again soon during another season to enjoy all it will have to offer.

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 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$195 - US$328 (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$195 - US$328 (Based on Average Rates for a Standard Room)
Also Known As
Great Oak Manor Hotel Chestertown
Location
United States > Maryland > Chestertown
Photos
Traveller (186)
Room & Suite (64)
Pool & Beach (14)
Dining (7)
Business Centre & Event Rooms (5)
Family and Play Areas (3)
Nearby
Nearby HotelsSee all 2 nearby hotels
Holiday Inn Express Hotel & Suites Chestertown
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12.34 km away
Quality Suites
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Tallulah's on Main
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Mariners Motel
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15.31 km away
Nearby RestaurantsSee all 51 restaurants in Chestertown
Luisa's Cucina Italiana
231 reviews
12.03 km away
Uncle Charlie's Bistro
173 reviews
12.24 km away
Cafe' Sado C-Town
38 reviews
11.90 km away
Procolino's Pizza
43 reviews
12.49 km away
Nearby AttractionsSee all 29 attractions in Chestertown
Experience Sail
11 reviews
3.49 km away
Carla Massoni Gallery
22 reviews
13.62 km away
Historical Society of Kent County
13 reviews
13.45 km away
Kent County Visitors Center
8 reviews
13.48 km away
Questions & Answers
Ask a question
Christopher G
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
"Marmaduke is spacious and light. Spectacular view of Bay. Comfortable chairs, huge bathroom, walk-in closet..."
Read review
"Rooms on the second floor west face the bay. A very good choice."
Read review
"The Tylden has a view of the bay with a small balcony."
Read review
"Roese Room is lovely and great for a family; Sterling Room is ground floor and is also good for a family."
Read review
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