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    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD 21620
    Hotel website
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    May 7
    May 8
    1 room, 2 adults, 0 children
    SAVE US$40
    US$305
    US$265
    US$305
    US$265
    Traveller (154)
    Room & Suite (40)
    Pool & Beach (12)
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    Overview

    • Excellent87%
    • Very good7%
    • Average2%
    • Poor1%
    • Terrible1%
    Travellers talk about
    “music room” (14 reviews)
    “private beach” (10 reviews)
    Free Wifi
    Free Parking
    Breakfast included
    Beachfront
    3.5 Star Hotel
    All hotel details
    Offers from Great Oak Manor
    Special Price: Buy 1 Night Get 1 Night
    Brampton Bed and Breakfast Inn
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    Rooms
    7 May8 May
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    1 room, 2 adults, 0 children
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    Write a Review
    Reviews (341)
    Traveller rating
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    1 - 5 of 341 reviews

    Reviewed 5 days ago

    Everything about this establishment is first class, and the fact that they have dog-friendly rooms is fantastic! The room has access to an outdoor garden area so you don't disturb other guests. I can't say enough about the friendliness of Holly, Richard and the entire...More

    Thank cbeenjammin
    Response from GREATOAKMANOR, Manager at Great Oak Manor

    Wow! Thank you for those wonderful words of praise for Great Oak Manor. We love our pets here so we hope you will visit with yours again real soon. Holly

    Reviewed 6 days ago via mobile

    Always love staying at the Great Oak Manor, especially this past 2-day visit as innkeeper Holly went way out of her way to accommodate my special dietary needs. She made delicious breakfasts for me each day and passed on to me her recipe for the...More

    Thank 1slowdancer
    Response from GREATOAKMANOR, Manager at Great Oak Manor

    Thank you for your kind words. We loved having you and don't mind a bit helping out anyone with special dietary needs. I am so grateful you enjoyed my offerings. I hope you have made the granola and are enjoying it at home. Hurry Back!!...More

    Reviewed 1 week ago

    My first bed and breakfast and now I'm spoiled. Beautiful, serene, property right on the water! The Inn was fabulous from the room accommodations, the staff, the food and the overall atmosphere. Kayaking, bike riding, and relaxing on the hammock by the water make this...More

    Thank Cheryl P
    Response from GREATOAKMANOR, Manager at Great Oak Manor

    Thank you Cheryl. We are so glad you first bed and breakfast experience was such a good one. We are looking forward to having you and Shana visit again. Holly

    Reviewed 2 weeks ago

    Simply outstanding B&B on the shores of the Chesapeake Bay, including - excellent hospitality from innkeepers Holly & Richard, thoughtful touches of unique services from breakfast through evening snacks & drinks to well-maintained common rooms and facilities. Grounds were in excellent shape as well, including...More

    Thank Kevin G
    Response from GREATOAKMANOR, Manager at Great Oak Manor

    Thank you Kevin. It was such a pleasure having you and Kristin stay with us. It thrills us to see our guests use the property and the access to the Bay. We look forward to you next visit. Holly

    Reviewed 2 weeks ago

    This is a wonderful location, right on the Chesapeake Bay on the Eastern Shore. The sunsets and views are spectacular and the setting can put your worries out of mind. The proximity to Chestertown, truly a hidden treasure with centuries of history and a thriving...More

    Thank Pennymohr
    Response from GREATOAKMANOR, Manager at Great Oak Manor

    Thank you Penny for your thoughts. Your points are well taken. Currently we serve breakfast between 9-10, soon to change to our summer hours of 8:30-10. It is a problem when everyone shows up at once on occasion. We had a full house this weekend...More

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    About
    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$189 - US$336 (Based on Average Rates for a Standard Room)
    • Hotel class
    • Room types
    • Suites ,
    • Non-Smoking Rooms ,
    • Family Rooms
    Photos
    Traveller (154)
    Room & Suite (40)
    Pool & Beach (12)
    Dining (3)
    Nearby
    Nearby Restaurants
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    Nearby Attractions
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    Questions & AnswersAsk a question
    Laurie A
    nightly rate
    6 April 2017|
    Answer Show 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
    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
    1
    Vote
    lmcoyle
    Recommendations for dining (breakfast, lunch or dinner) in this area?
    25 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
    2
    Votes
    Room Tips
    "They do have dog-friendly rooms available."
    Read review
    "the website does not do the rooms justice. All have a little different flair."
    Read review
    "Geddes Piper is charming! But I'm sure they are all awesome!"
    Read review
    "Ask for a water view, although you probably will enjoy the grounds one way or the other."
    Read review