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01/10/2017 02/10/2017
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    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD 21620-4115
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    01/10/2017 02/10/2017
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    US$169
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    Traveller (164)
    Room & Suite (41)
    Pool & Beach (13)
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    Overview
    • Excellent90%
    • Very good7%
    • Average1%
    • Poor1%
    • Terrible1%
    Travellers 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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    Brampton Bed and Breakfast Inn
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    #1 of 11 B&Bs / Inns in Chestertown
     
    The Inn at Osprey Point
    333 reviews
    #1 of 10 B&Bs / Inns in Rock Hall
     
    Holiday Inn Express Hotel & Suites Chestertown
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    Rooms
    1 Oct2 Oct
    |
    1 room, 2 adults, 0 children
    Standard Room

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    Standard Room

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    Write a Review
    Reviews (373)
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    1 - 5 of 373 reviews

    Reviewed 6 days ago via mobile

    The setting, the staff, and of course the Manor are all great. If you need to get away from it all, come here. Both husbands and wives can be happy here. The Bay is beautiful, golfing and sailing close by, bikes provided, and plenty of...More

    Thank FmrInnKeep
    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 via mobile

    We had the privilege of staying here for two nights. Lynn graciously welcomed us at the front door and the rest of our time reflected this first impression. We stayed in the spacious Marmaduke room which offers a lovely view of the grounds and the...More

    Thank missourifarmgirl
    Management response:Responded 6 days ago

    We are so glad to hear of your wonderful stay. Our staff is the best and we appreciate your kind words. So sorry to have missed you ourselves.

    Reviewed 2 weeks ago

    This was our second time staying here with daughter and dog. We went for a mid-week BOGO two-night stay in early August. The Good: The property is lovely. Sitting high above the water it features gorgeous views of Chesapeake Bay, with a small beach and...More

    Thank Paul R
    Reviewed 3 weeks ago

    Beautiful grounds, quiet, peaceful, tranquil. Wonderful hospitality from innkeepers, Holly, Richard and Miss Lizzy! Entire staff is amazing! Felt very welcome by all. The Manor is a true piece of history, so well preserved and comfortable. The public and private rooms are immaculate.

    Thank jrb1412016
    Response from Holly M, Manager at Great Oak ManorResponded 3 weeks ago

    Thank you for your wonderful review. It makes us so happy when our guests "get" this place. It is truly special in so many ways. We look forward to your next stay of relaxation here-hope it is sooner.

    Brampton Bed and Breakfast Inn
    646 reviews
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    The Inn at Osprey Point
    333 reviews
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    Holiday Inn Express Hotel & Suites Chestertown
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    Inn at Huntingfield Creek
    319 reviews
    #2 of 10 B&Bs / Inns in Rock Hall
     
    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
    • US$186 - US$313 (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, Priceline, Expedia, Hotels.com, Travelocity, Orbitz, Cancelon, Hotwire and Cheap Tickets 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 (164)
    Room & Suite (41)
    Pool & Beach (13)
    Dining (3)
    Hotel & Grounds (128)
    Family and Play Areas (3)
    Business Centre & Event Rooms (2)
    Nearby
    Nearby Restaurants
    Lemon Leaf Cafe
    580 reviews
    13.32 km away
    Luisa's Cucina Italiana
    193 reviews
    12.06 km away
    Fords Seafood
    56 reviews
    13.14 km away
    Uncle Charlie's Bistro
    154 reviews
    12.23 km away
    Nearby Attractions
    Experience Sail
    11 reviews
    3.48 km away
    Carla Massoni Gallery
    20 reviews
    13.61 km away
    Blue Crab Chesapeake Charters
    272 reviews
    14.81 km away
    Historical Society of Kent County
    10 reviews
    13.63 km away
    Ask a question
    Questions & Answers
    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
    0
    Votes
    LKenney07
    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
    1
    Vote
    lmcoyle
    26 February 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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