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2/4/2018 2/5/2018
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    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD 21620-4115
    +1 800-504-3098
    Hotel website
    Lowest prices for your stay
    2/4/2018 2/5/2018
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    Traveler (175)
    Room & Suite (48)
    • Excellent90%
    • Very good7%
    • Average1%
    • Poor1%
    • Terrible1%
    Travelers talk about
    “chesapeake bay” (76 reviews)
    “music room” (14 reviews)
    “private beach” (12 reviews)
    Free Wifi
    Free Parking
    Breakfast included
    Air Conditioning
    Non-Smoking Hotel
    Pets Allowed
    Accessible rooms
    3.5 Star Hotel
    All hotel details
    Offers from Great Oak Manor
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    Feb 4Feb 5
    1 room, 2 adults, 0 children
    Standard Room

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    Standard Room

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    Write a ReviewReviews (385)
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    1 - 5 of 385 reviews

    Reviewed 1 week ago

    We stayed at the Great Oak Manor for my son's wedding (at the Manor as well). We stayed in the Carriage House and it was great! Richard and Holly McKee were awesome! Anything we needed or questions they had were promptly taken care of for...More

    Thank TJ E
    Response from GREATOAKMANOR, Manager at Great Oak ManorResponded 1 week ago

    We appreciate all of our guests, but we especially appreciate your kind remarks during your visit. It was our pleasure having all of you here and we are so glad you enjoyed the wedding and your entire stay. I realize you live too far away...More

    Innkeeper's Favorite Review
    Reviewed May 30, 2017

    My husband and I had our 50th Wedding Anniversary planned for the week of May 20th in Newport. RI, where we met and were married. However, I had a stroke instead, so all of our plans had to be cancelled. Our friends had recently been...More

    2  Thank rhodyred
    Response from GREATOAKMANOR, Manager at Great Oak ManorResponded June 7, 2017

    You know when we learned of your stroke and the cancellation of your plans, we knew we needed to make this a special time for the two of you. It is soooo easy to do that for kind and wonderful guests, such as yourself. You...More

    Reviewed 3 weeks ago

    A few girlfriends and I stayed in the Cottage while hunting Canada Geese for a few days. I must say I felt like I was spoiled!! The manor on it's own just has so much elegance and history to it, but the Cottage that was...More

    Thank RachelleH164
    Response from General M, Manager at Great Oak ManorResponded 3 weeks ago

    Now you all were a fun bunch of young women. It was our pleasure to meet you and we can't wait to see you again. Thank you for all the nice things you said and we are so glad you described your stay in the...More

    Reviewed 3 weeks ago

    Christmas was very merry and bright at Great Oak Manor! All the guests enjoyed a delicious Christmas dinner with great wine and a crackling fire in the dining room (dinner was free if you stayed there at least three nights!). We laughed a lot and...More

    Thank FlowerLady27
    Response from Holly M, Manager at Great Oak ManorResponded 3 weeks ago

    Thank you for your kind and generous accolades. We enjoyed having everyone here for the holiday and hope you will consider returning next year (if not before.)

    Reviewed 4 weeks ago

    I really cannot say enough about this wonderful manor. My bride and I just got back from our incredible visit this past weekend. From the start to the finish this could not have been a better experience. I will start by praising the manor itself...More

    Thank mountarchitecture
    Response from Holly M, Manager at Great Oak ManorResponded 3 weeks ago

    Wow! I want to stay at this place. Ha! You articulated perfectly all the best things about staying here. Richard and I humbly accept your praise. We thoroughly enjoy our guests and getting to know them. You became friends of the Manor and of us...More

    Awards & Recognition
    GreenLeadersGold level
    Certificate of Excellence
    • Top amenities
    • Free Parking
    • Free High Speed Internet ( WiFi )
    • Breakfast included
    • Beachfront
    • Hotel Amenities
    • Free Parking
    • Breakfast included
    • Room amenities
    • Air Conditioning
    • Price range
    • $153 - $257 (Based on Average Rates for a Standard Room)
    • Hotel class
    • Room types
    • Suites ,
    • Non-Smoking Rooms ,
    • Family Rooms ,
    • Accessible rooms
    • Number of rooms
    • 13
    • Reservation Options
    • TripAdvisor is proud to partner with Expedia, Hotels.com, Travelocity, Booking.com, Orbitz and Cancelon so you can book your Great Oak Manor reservations with confidence. We help millions of travelers each month to find the perfect hotel for both vacation and business trips, always with the best discounts and special offers.
    • Location
    • United States >
    • Maryland >
    • Chestertown
    • Also Known As
    • Great Oak Manor Hotel Chestertown
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    Traveler (175)
    Room & Suite (48)
    Pool & Beach (13)
    Dining (3)
    Hotel & Grounds (133)
    Business Center & Event Rooms (6)
    Family and Play Areas (3)
    Bathroom (2)
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    Ask a question
    Questions & Answers
    Christopher G
    October 4, 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
    Laurie A
    April 6, 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
    October 20, 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
    Room Tips
    "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
    "They are all great from what I can tell. We stayed in the 'D'Oench' room."
    Read review
    "Get a bay view. Well worth it."
    Read review
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