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    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD 21620-4115
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    8/6/2017 8/7/2017
    $247
    $247
    $247
    Traveler (160)
    Room & Suite (41)
    Pool & Beach (13)
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    Overview
    • Excellent90%
    • Very good7%
    • Average1%
    • Poor1%
    • Terrible1%
    Travelers talk about
    “music room” (14 reviews)
    “private beach” (11 reviews)
    Free Wifi
    Free Parking
    Breakfast included
    Air Conditioning
    Beachfront
    Non-Smoking Hotel
    Suites
    Pets Allowed
    Pool
    3.5 Star Hotel
    All hotel details
    Offers from Great Oak Manor
    Offers & Announcements: 1 FREE NIGHT🆓CLICK HERE
    Holiday Inn Express Hotel & Suites Chestertown
    146 reviews
    #1 of 2 hotels in Chestertown
     
    Hampton Inn & Suites Edgewood/Aberdeen-South
    596 reviews
    #1 of 9 hotels in Edgewood
     
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    115 reviews
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    Rooms
    Aug 6Aug 7
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    1 room, 2 adults, 0 children
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    Write a Review
    Reviews (361)
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    1 - 5 of 361 reviews

    Reviewed 2 days ago

    I normally do not review hotels but,,, While we have revisited this property a few times, it remains very special to us all in our family for its unique presence over the Bay and it architecture and wonderful inn keepers Holy, Richard and Lyn. Our...More

    Thank emfrealty
    Response from GREATOAKMANOR, Manager at Great Oak ManorResponded yesterday

    Thank you so much for your kind words. We strive to make all of our guests feel special and want them to enjoy everything about this amazing property. We are definitely looking forward to your next visit.

    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 1 week 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 6 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

    Reviewed 2 weeks 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 2 weeks 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 2 weeks 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

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    About
    Awards & Recognition
    GreenLeadersGold level
    Certificate of Excellence
    Amenities
    • Top amenities
    • Free Parking
    • Breakfast included
    • Beachfront
    • Free High Speed Internet ( WiFi )
    • Hotel Amenities
    • Free Parking
    • Breakfast included
    • Room amenities
    • Air Conditioning
    Details
    • Price range
    • $263 - $328 (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, Priceline, Hotels.com, Orbitz, Cancelon, Travelocity and Hotwire 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 (160)
    Room & Suite (41)
    Pool & Beach (13)
    Dining (3)
    Hotel & Grounds (124)
    Family and Play Areas (3)
    Business Center & Event Rooms (2)
    Nearby
    Sponsored by:
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    7.66 miles away
     
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    7.68 miles away
     
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    20.72 miles away
     
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    Nearby Restaurants
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    8.28 miles away
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    7.49 miles away
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    7.60 miles away
    Fords Seafood
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    8.16 miles away
    Nearby Attractions
    Experience Sail
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    2.34 miles away
    Carla Massoni Gallery
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    8.46 miles away
    Blue Crab Chesapeake Charters
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    Ask a question
    Questions & Answers
    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
    0
    Votes
    LKenney07
    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
    1
    Vote
    lmcoyle
    February 25, 2015|
    AnswerShow 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
    2
    Votes
    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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