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09/04/2017 10/04/2017
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    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD 21620
    Hotel website
    Apr 9 Apr 10
    1 room, 2 adults, 0 children
    View Deal
    Traveller (141)
    Room & Suite (38)
    Pool & Beach (12)

    • Excellent87%
    • Very good7%
    • Average2%
    • Poor1%
    • Terrible1%
    Travellers talk about
    “music room” (14 reviews)
    Free Wifi
    Free Parking
    Breakfast included
    3.5 Star Hotel
    All hotel details
    09/04/2017 10/04/2017
    Standard Room

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    Free Cancellation
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    Standard Room

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    Free Cancellation
    09/04/2017 10/04/2017
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    Traveller rating
    Traveller type
    Time of year
    All reviews chesapeake bay music room view of the bay private beach adirondack chairs breathtaking views fire pit scott sunset port library lawn innkeepers grounds conservatory sherry shore mansion
    Reviewed 6 days ago

    We were very impressed with the magnificent rooms in the Manor. The view of the water was great. We managed to catch the sunset that evening. Vincent told us we could have a fire in our room, so we did. It was cozy and warm...More

    Reviewed 2 weeks ago

    What a lovely spot on the Chesapeake! We enjoyed a quick stay of just one night last week, and had the whole place to ourselves. We went exploring and got to see all of the beautifully-decorated rooms, each one unique. Vincent took great care of...More

    Response from GREATOAKMANOR, General Manager at Great Oak Manor

    The few times we ever get to have only one couple for an evening, we try to provide the "Lord and Lady of the Manor" experience. We are glad we had the chance to make your stay so memorable. Thank you so much for acknowledging...More

    Reviewed 20 February 2017 via mobile

    Incredible customer service and a hidden gem on the water. So gorgeous and relaxing. It was so nice to get away from the city and escape. Highly recommend! The Caulk room was incredible:) The decor was so nice and I felt right at home as...More

    Response from GREATOAKMANOR, Manager at Great Oak Manor

    "I felt right at home..." is what we strive for and hope all our guests feel. The little balcony off the Caulk room is a nice, private place to drink some wine and watch the sunset. I'll bet you did that! Thank you for the...

    Reviewed 16 February 2017

    We love the manor. It is elegant and refined with first class service. Everyone is friendly and trying to make your stay a wonderful experience. I recommend that you visit their website and view all the rooms. Keep in mind that this is not a...More

    Response from GREATOAKMANOR, Manager at Great Oak Manor

    Thank you for your gracious response. We are glad you took the opportunity to explore all the rooms in the Manor. Our various common rooms give our guests the ability to escape, unwind and relax. If you had been here just a couple days later,...More

    Reviewed 14 February 2017

    This was our second visit to The Great Oak Manor in Chestertown. We highly recommend this B&B to all couples. The magnificent accommodations and panoramic view could only be topped by the courteous service. It may be a bit out of the way, but it...More

    Response from GREATOAKMANOR, Manager at Great Oak Manor

    We are so glad you had a chance to visit us and enjoy your Valentine's Day and anniversary escape. Special times call for special places and we are happy to help our guests celebrate these occasions. Thank you for your wonderful response. We hope to...

    • Top amenities
    • Free Parking
    • Breakfast included
    • Beachfront
    • Free High Speed Internet ( WiFi )
    • Hotel Amenities
    • Free Parking
    • Breakfast included
    • Room amenities
    • Air Conditioning
    Traveller (141)
    Room & Suite (38)
    Pool & Beach (12)
    Dining (2)
    Nearby Restaurants
    Lemon Leaf Cafe
    542 reviews
    13.34 km away
    Luisa's Cucina Italiana
    178 reviews
    12.07 km away
    Uncle Charlie's Bistro
    140 reviews
    12.24 km away
    Fords Seafood
    45 reviews
    13.15 km away
    Nearby Attractions
    Experience Sail
    11 reviews
    3.77 km away
    Carla Massoni Gallery
    15 reviews
    13.62 km away
    Blue Crab Chesapeake Charters
    248 reviews
    14.82 km away
    Historical Society of Kent County
    10 reviews
    13.64 km away
    Questions & AnswersAsk a question
    Planning an overnight stay for an anniversary. Does this establishment accommodate LGBT guests?
    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
    Recommendations for dining (breakfast, lunch or dinner) in this area?
    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
    "Some rooms have a view of the water."
    Kathy W, 5 days agoRead review
    "Corner rooms on the 2nd floor have great views!"
    USVI_BVI_Traveler, 19 days agoRead review
    "Most rooms face the water. Perhaps one or two do not."
    surferboyMaryland, 1 month agoRead review
    "Best advise, go to another BnB in Chestertown"
    Tim G, 1 month agoRead review
    "Wait to book because they will drop the rate or give you half off"
    bobindc43, 3 months agoRead review
    "Do not book a room on the third floor. Too far up and in need of updating."
    RoHoehler, 4 months agoRead review
    "D'Oench is a large room with a good view but no balcony. Caulk has the same view, it's a little..."
    Bob W, 5 months agoRead review
    "Russel room fantastic"
    chemistandnurse, 5 months agoRead review
    "Every room is beautiful"
    frequentflyer3343, 6 months agoRead review
    "Best with view of Chester River."
    Kellw622, 6 months agoRead review
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