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    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD 21620-4115
    +1 855-338-2248
    Hotel website
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    Lowest prices for your stay
    -- / -- / --Check In -- / -- / --Check Out
    1 room, 2 adults, 0 children
    US$ 194
    US$ 169
    SAVE US$ 25
    US$ 194
    US$ 169
    Traveller (165)
    Room & Suite (42)
    Pool & Beach (13)
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    Overview
    • Excellent90%
    • Very good7%
    • Average1%
    • Poor1%
    • Terrible1%
    Travellers talk about
    “chesapeake bay” (76 reviews)
    “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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    Rooms
    5 Nov6 Nov
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    1 room, 2 adults, 0 children
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    Reviews (376)
    Traveller rating
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    1 - 5 of 376 reviews

    Reviewed 1 week ago

    The property is absolutely gorgeous, and the innkeepers, Holly and Richard, tended to every detail to make my stay as relaxing and restorative as possible! The common spaces are both gracious and welcoming, and the view of the bay is just stunning. I will be...More

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

    Thank you Gini. We are so glad to here your stay was restorative for you. This is a special place and we love it when our guests realize it as well. We look forward to your next visit.

    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

    D'Oench Room was sop spacious and comfortable. Better yet was Holly, the innkeeper who had a million dollar personality. Her chickens provided fresh eggs produced one of my very best breakfasts. Holly also makes her own granola that was something extra special and a wonderful...More

    Thank regina187
    Response from Holly M, Manager at Great Oak ManorResponded 1 week ago

    Thank you for your kind comments. It is always a pleasure and very easy to be with such nice guests. We do indeed hope you will return at your earliest convenience.

    Reviewed 2 weeks ago

    We absolutely loved our stay at Great Oak Manor!  The grounds were beautiful and the bay in walking distance; was great for fishing!  The Carriage House was a wonderful accommodation, so comfortable and spacious!  The breakfasts prepared were delicious, the peach homemade muffins were excellent! ...More

    Thank model99
    Response from Holly M, Manager at Great Oak ManorResponded 2 weeks ago

    Thank you all for your wonderful review. We are so pleased to hear of your great experience. Our interim staff has a lot of experience and do a fantastic job so all guests will know no difference in our absence. We hope you will return...More

    Reviewed 17 September 2017 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
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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
    • US$ 167 - US$ 219 (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, Travelocity, Orbitz, Cheap Tickets, Hotwire 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
    Add Photo Photos
    Traveller (165)
    Room & Suite (42)
    Pool & Beach (13)
    Dining (3)
    Hotel & Grounds (128)
    Family and Play Areas (3)
    Business Centre & Event Rooms (2)
    Nearby
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    23.69 km away
     
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    24.91 km away
     
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    Hilton Garden Inn Aberdeen
    468 reviews
    28.02 km away
     
    Nearby Restaurants
    Lemon Leaf Cafe
    593 reviews
    13.34 km away
    Luisa's Cucina Italiana
    196 reviews
    12.06 km away
    Uncle Charlie's Bistro
    156 reviews
    12.23 km away
    Fords Seafood
    58 reviews
    13.14 km away
    Nearby Attractions
    Experience Sail
    11 reviews
    3.48 km away
    Carla Massoni Gallery
    20 reviews
    13.61 km away
    Historical Society of Kent County
    10 reviews
    13.63 km away
    Garfield Center for the Arts at the Prince Theatre
    6 reviews
    13.59 km away
    Ask a question
    Questions & Answers
    Christopher G
    4 October 2017|
    AnswerShow all 4 answers
    Response from Emmett4640 | Reviewed this property |
    Scenery and wildlife at and near Great Oak is good but can't speak to what it's like in December. The Inn is five miles outside of town. Chestertown has nice shops and a great bookstore, but some stores and restaurants might... More
    0
    Votes
    Laurie A
    6 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
    Room Tips
    "If you're going to Chesapeake Bay, pick a room with a view of the bay. It is to die for!"
    Read review
    "Carriage House at Great Oak Manor is superb!"
    Read review
    "2nd floor corner rooms are very nice"
    Read review
    "We were in the Wickes and Sterling Suites - both were comfortable and clean."
    Read review
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