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31/12/2017 01/01/2018
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    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD 21620-4115
    +1 855-338-2248
    Hotel website
    Lowest prices for your stay
    31/12/2017 01/01/2018
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    Traveller (169)
    Room & Suite (44)
    • Excellent90%
    • Very good7%
    • Average1%
    • Poor1%
    • Terrible1%
    Travellers 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
    Special Price: BOGO on 2 nights
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    31 Dec.1 Jan.
    1 room, 2 adults, 0 children
    Standard Room

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    Standard Room

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    Free Cancellation
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    Write a ReviewReviews (381)
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    1 - 5 of 381 reviews

    Reviewed yesterday

    The Manor was well worth the trip to get there. The building and grounds are magnificent. There is a wonderful bird sanctuary nearby. The hosts, Holly and Richard, made sure that we had a great time. It is now our favorite getaway spot.

    Thank Mike J
    Innkeeper's Favourite Review
    Reviewed 30 May 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 8 June 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 1 week ago

    We had our wedding at GOM on the weekend of October 14th. My comments here are not about GOM as a wedding venue - but instead as a place to visit for a relaxing and peaceful vacation to get away from it all. The house...More

    Thank bfeeley1982
    Response from General M, Manager at Great Oak ManorResponded 1 week ago

    And it was a beautiful wedding! I laugh about the "middle of nowhere" as we are at the end of farm country lanes right on the Chesapeake Bay. The original owner of the Manor knew what he was doing by designing a mansion and situating...More

    Reviewed 11 November 2017

    There are not enough positive words available to explain how perfect our wedding weekend was at Great Oak Manor. Our September wedding went beautifully with the help of the staff at Great Oak. Our family booked the manor for Friday-Sunday so we could enjoy having...More

    Thank Jessica R
    Response from General M, Manager at Great Oak ManorResponded 5 weeks ago

    Thank you so much for your kind words Jessica. It is especially gratifying to know our brides are so pleased with their choice of Great Oak Manor as their wedding venue. We have an exceptional staff and are pleased they performed so well for you....More

    Reviewed 7 November 2017

    My husband and I spent our 44th wedding anniversary at Great Oak Manor this past weekend. It was a most memorable occasion. The Inn was lovely, the breakfast wonderful, but the best part of the stay was getting acquainted with Holly and Richard, the Inn...More

    Thank szeigler4te
    Response from General M, Manager at Great Oak ManorResponded 8 November 2017

    Thank you, Sharon, for your kind words. It is always a pleasure to extend hospitality to wonderful and friendly guests. We did enjoy meeting you both so much and look forward to your next visit in warmer weather.

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    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
    • USD 156 - USD 265 (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 Hotwire, Expedia, Travelocity, Hotels.com, Booking.com, Priceline, Orbitz and Cancelon so you can book your Great Oak Manor reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday 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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    Traveller (169)
    Room & Suite (44)
    Pool & Beach (13)
    Dining (3)
    Hotel & Grounds (131)
    Business Centre & Event Rooms (6)
    Family and Play Areas (3)
    Bathroom (2)
    Nearby Restaurants
    Lemon Leaf Cafe
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    13.34 km away
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    203 reviews
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    61 reviews
    13.14 km away
    Cafe' Sado C-Town
    32 reviews
    11.89 km away
    Nearby Attractions
    Experience Sail
    11 reviews
    3.48 km away
    Carla Massoni Gallery
    21 reviews
    13.61 km away
    Historical Society of Kent County
    10 reviews
    13.63 km away
    Kent County Visitors Center
    6 reviews
    13.47 km away
    Ask a question
    Questions & Answers
    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
    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
    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
    Room Tips
    "Get a bay view. Well worth it."
    Read review
    "If you're going to Chesapeake Bay, pick a room with a view of the bay. It is to die for!"
    Read review
    "Carriage House at Great Oak Manor is superb!"
    Read review
    "2nd floor corner rooms are very nice"
    Read review
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