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06/08/2017 07/08/2017
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    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD 21620-4115
    Hotel website
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    06/08/2017 07/08/2017
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    Traveller (160)
    Room & Suite (41)
    Pool & Beach (13)
    • Excellent90%
    • Very good7%
    • Average1%
    • Poor1%
    • Terrible1%
    Travellers talk about
    “music room” (14 reviews)
    “private beach” (11 reviews)
    Free Wifi
    Free Parking
    Breakfast included
    Air Conditioning
    Non-Smoking Hotel
    Pets Allowed
    3.5 Star Hotel
    All hotel details
    Offers from Great Oak Manor
    Offers & Announcements: 1 FREE NIGHT🆓CLICK HERE
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    6 Aug7 Aug
    1 room, 2 adults, 0 children
    Standard Room

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    Standard Room

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    Write a Review
    Reviews (360)
    Traveller rating
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    Time of year

    1 - 5 of 360 reviews

    Reviewed 4 days ago

    We highly recommend this B&B for a stay in the Chestertown area. We stayed at Great Oak Manor for three nights in June. We travel with a child who has a food allergy, and the owners were very accommodating of his situation, for which we...More

    Thank KatieinBoston
    Response from Holly M, Manager at Great Oak ManorResponded 2 days ago

    Thank you for your kind words of our Manor and our staff. We are very lucky to have such a beautiful to live and work. I am so glad you spoke up about the temperature of your room as we want all of our guests...More

    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

    What a wonderful place for our first visit to the Chesapeake Bay. The comfortable room, delicious breakfasts, and beautiful sunsets were most enjoyable. We liked shopping in quaint Chestertown. There was a farmer's market in the town square the Saturday morning we were there. We...More

    Thank wncmtngrl
    Response from Holly M, Manager at Great Oak ManorResponded 1 week ago

    We are so glad to hear you had such a wonderful visit on your first visit to Chesapeake country. Don't forget the way here as we want to see you again very soon. Thanks for the kind words. Holly

    Reviewed 1 week ago

    The upside to Great Oak Manor being a 20 minute drive from Chestertown is that guest enjoy a large, beautiful property, including a tiny private beach, hammocks and magnificent sunsets. The inn is beautifully appointed. It feels like a chateau in the French countryside. Breakfast...More

    Thank VC1850
    Response from GREATOAKMANOR, Manager at Great Oak ManorResponded 1 week ago

    So glad you enjoyed your stay and appreciated the beauty of this area. We are, indeed, fortunate to live here and love sharing it with our guests. We hope to see you again in the near future. Holly

    Reviewed 2 weeks ago

    My wife and I escaped to the Great Oak Manor as a reward for graduating our youngest from High School. We spent four lovely days at the beautiful Great Oak Manor. Holly and Richard are amazing. So warm, welcoming and knowledgeable. We stayed in the...More

    Thank Mel W
    Response from GREATOAKMANOR, Manager at Great Oak ManorResponded 1 week ago

    Thank you Mel. It was our pleasure to have you both stay with us. We appreciate your kind words and notice of our efforts. We can't wait for your return and hope it won't be four years! Holly

    Awards & Recognition
    GreenLeadersGold level
    Certificate of Excellence
    • Top amenities
    • Free Parking
    • Breakfast included
    • Beachfront
    • Free High Speed Internet ( WiFi )
    • Hotel Amenities
    • Free Parking
    • Breakfast included
    • Room amenities
    • Air Conditioning
    • Price range
    • US$264 - US$333 (Based on Average Rates for a Standard Room)
    • Hotel class
    • Room types
    • Suites ,
    • Non-Smoking Rooms ,
    • Family Rooms
    • Number of rooms
    • 12
    • Reservation Options
    • TripAdvisor is proud to partner with Booking.com, Expedia, Orbitz, Hotels.com, Hotwire, Cheap Tickets, Travelocity, Cancelon and Priceline 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 (160)
    Room & Suite (41)
    Pool & Beach (13)
    Dining (3)
    Hotel & Grounds (124)
    Family and Play Areas (3)
    Business Centre & Event Rooms (2)
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    Ask a question
    Questions & Answers
    Laurie A
    7 April 2017|
    Answer Show 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|
    Answer Show 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
    26 February 2015|
    Answer Show all 2 answers
    Response from GREATOAKMANOR | Property representative |
    Hi there! If you choose to stay with us at Great Oak Manor Inn, you'll get a full breakfast with fresh seasonal fruit, cereal, yogurt, homemade baked goods, breakfast meat, and a hot entrée (French toast, eggs to order... More
    Room Tips
    "Marmaduke have a great view of the Bay."
    Read review
    "Third floor"
    Read review
    "Bay views from rooms along the back of the manor"
    Read review
    "Ask for a bay view room"
    Read review
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