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    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD 21620-4115
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    10/1/2017 10/2/2017
    $172
    $172
    $172
    Traveler (164)
    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” (12 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
    Special Rate: Fall Room Specail
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    Holiday Inn Express Hotel & Suites Chestertown
    151 reviews
    #1 of 2 hotels in Chestertown
     
    Quality Suites
    117 reviews
    #2 of 2 hotels in Chestertown
     
    Best Western Plus Hotel & Conference Center
    1,215 reviews
    #38 of 67 hotels in Baltimore
     
    Inn at Henderson's Wharf
    990 reviews
    #2 of 67 hotels in Baltimore
     
    Rooms
    Oct 1Oct 2
    |
    1 room, 2 adults, 0 children
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    Standard Room

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    Write a Review
    Reviews (373)
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    121 - 125 of 373 reviews

    Reviewed May 2, 2016

    The location is remote enough to be very relaxing, while close enough to Chestertown that you won't feel cut off from "civilization." The breakfasts were fantastic -- they were happy to accommodate my wife's vegetarianism, including using veggie bacon, which was really unexpected. Innkeeper Kaylin...More

    Review collected in partnership with this hotel
    Thank michael_a_marsh
    Response from GOMStaff, General Manager at Great Oak ManorResponded May 5, 2016

    Hi Michael, It was such a pleasure to meet both yourself and your wife. We were so pleased that you were able to enjoy the kayaks and paddle boards and I appreciate the compliments on my cookies! We certainly hope that you will come back...More

    Reviewed April 22, 2016

    We had a terrific weekend at Great Oak Manor. It was a last minute trip and I was really happy we did it. The grounds of the Manor are really nice. We saw eagles and a beautiful sunset, and the farmers market in nearby Chestertown...More

    Review collected in partnership with this hotel
    Thank rebl324
    Response from GOMStaff, General Manager at Great Oak ManorResponded May 2, 2016

    It is so wonderful to hear that you enjoyed your stay at the Manor and were able to roam our 12 acres as well as see the eagles and a great sunset. We do hope that you will come back and visit us again soon....More

    Reviewed April 21, 2016

    Amazing Place - Amazing Staff - Amazing Food- Amazing Sunsets...Golfed, played croquet, Bago, hung out in hammocks, bird watched, paddle boarded and so much more! The property is surrounded by fun things to do and they even organized a sailing trip for us - amazing!More

    Review collected in partnership with this hotel
    Thank Victoria C
    Response from GOMStaff, General Manager at Great Oak ManorResponded May 2, 2016

    Hi Victoria, We are so happy to know that you enjoyed your stay. You really made the most of all the amenities and we are so thrilled that you were able to take advantage of all that we have available to our guests. We hope...More

    Reviewed April 20, 2016

    This trip was absolutely amazing my wife and I had not had a weekend alone for almost a year since we moved to Maryland and I have to say this place is amazing from the house to the innkeepers. It was just so peaceful and...More

    Review collected in partnership with this hotel
    Thank Juan P
    Response from GOMStaff, General Manager at Great Oak ManorResponded April 21, 2016

    Hi Juan, we are so delighted that you enjoyed your stay with us. The next time you are looking for a getaway we hope that you will think of us! Kaylin Benfield Innkeeper

    Reviewed April 14, 2016

    Gluten-free accomodations made. We had requested twin beds but the beds were together when we arrived. By the time we got back from dinner, beds were in correct position. This place is not near town, so you will feel "out in the country" - very...More

    Thank BARBARA F
    Holiday Inn Express Hotel & Suites Chestertown
    151 reviews
    #1 of 2 hotels in Chestertown
     
    Quality Suites
    117 reviews
    #2 of 2 hotels in Chestertown
     
    Best Western Plus Hotel & Conference Center
    1,215 reviews
    #38 of 67 hotels in Baltimore
     
    Inn at Henderson's Wharf
    990 reviews
    #2 of 67 hotels in Baltimore
     
    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
    • $186 - $314 (Based on Average Rates for a Standard Room)
    • Hotel class
    • Room types
    • Suites ,
    • Non-Smoking Rooms ,
    • Family Rooms
    • Number of rooms
    • 13
    • Reservation Options
    • TripAdvisor is proud to partner with Booking.com, Expedia, Hotels.com, Priceline, Travelocity, Orbitz, Cancelon, Hotwire and Cheap Tickets 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
    Add Photo Photos
    Traveler (164)
    Room & Suite (41)
    Pool & Beach (13)
    Dining (3)
    Hotel & Grounds (128)
    Family and Play Areas (3)
    Business Center & Event Rooms (2)
    Nearby
    Sponsored by:
    Holiday Inn Express Hotel & Suites Chestertown
    151 reviews
    7.70 miles away
     
    Quality Suites
    117 reviews
    7.69 miles away
     
    Best Western Plus Hotel & Conference Center
    1,215 reviews
    18.46 miles away
     
    Inn at Henderson's Wharf
    990 reviews
    20.71 miles away
     
    Nearby Restaurants
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    Fords Seafood
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    8.17 miles away
    Uncle Charlie's Bistro
    154 reviews
    7.61 miles away
    Nearby Attractions
    Experience Sail
    11 reviews
    2.17 miles away
    Carla Massoni Gallery
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    8.47 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
    "2nd floor corner rooms are very nice"
    Read review
    "We were in the Wickes and Sterling Suites - both were comfortable and clean."
    Read review
    "Marmaduke have a great view of the Bay."
    Read review
    "Third floor"
    Read review
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