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“A Fond Goodbye, Cassandra”
5 of 5 bubbles Review of Great Oak Manor

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Great Oak Manor
Ranked #2 of 11 Chestertown B&B and Inns
Certificate of Excellence
GreenLeadersGold level
Allentown, PA
Level Contributor
12 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 12 helpful votes
“A Fond Goodbye, Cassandra”
5 of 5 bubbles Reviewed May 13, 2012

We were saddened to learn that the inn would no longer be under your expert management, and want to let you know that we were glad that we were at Great Oak for the final weekend. It's been so wonderful visiting with you and John at the inn, and we will most certainly miss your outstanding service and the warm friendship you've extended to us again and again throughout the year. Take good care of your golden co-host, Charly. We will miss his happy greeting as well!

  • Stayed April 2012, traveled as a couple
    • Service
Helpful?
2 Thank Brentana
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
GreatOakJohn, Owner at Great Oak Manor, responded to this review, May 28, 2012
We were so honored you were there for our final weekend. Enduring relationships with our guests have made this 10 year experience precious to us. John and I want to thank you and everyone who has taken the time to write and share your experiences at Great Oak Manor on tripadvisor. It truly has been our pleasure to meet all of you and provide you with the gracious hospitality that we have always aspired to achieve.
We will miss all of you and wish you all the best.
Cassandra and John Fedas
Charly the golden
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
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341 reviews from our community

Traveler rating
    298
    26
    7
    4
    6
See reviews for
56
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Rating summary
  • Location
    5 of 5 bubbles
  • Sleep Quality
    5 of 5 bubbles
  • Rooms
    4.5 of 5 bubbles
  • Service
    5 of 5 bubbles
  • Value
    4.5 of 5 bubbles
  • Cleanliness
    5 of 5 bubbles
Traveler tips help you choose the right room.   Room tips (72)
Date | Rating
  • English first
  • Any
English first
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 bubbles Reviewed March 26, 2012

The gracious hospitality offered by Innkeeper Casssandra and her sweet golden retriever Charlie was rivaled onky by the jaw-dropping view from the back garden of this beautiful waterfront estate. The vibe is one of easy-going elegance, and every need and detail was attended to. We slept like babies, filled our bellies with yummy breakfasts, and our big lug of a dog Hunter was treated like a king. It was hard to leave.

  • Stayed March 2012
    • Value
    • Location
    • Rooms
    • Cleanliness
    • Service
Helpful?
1 Thank RLorraine
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Level Contributor
5 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed March 18, 2012 via mobile

My husband and I just returned from a wonderful, rejuvenating long weekend at the Great Oak Inn. We were looking for a special place to celebrate our 26th wedding anniversary and this was just the spot. The Inn was magnificent and Cassandra and staff were most accommodating. Breakfast and snacks were very tasty. We had the Bay view to ourselves the first night and loved the spectacular sunset and quiet. We spent the day light hours exploring Chestertown, Rock Fall, and the Eastern Shore Wildlife Preserve. We had dinner at two completely different but spectacular restaurants. After breakfast this morning, we took a walk around the spectacular property and surrounding area. The hillside covered in yellow and white daffodils brought out the photographer in me. We headed home knowing that we will visit again soon!

Stayed March 2012
Helpful?
Thank elura66
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Beaverdam, Virginia
1 review
5 of 5 bubbles Reviewed March 5, 2012

My husband and I were looking for a relaxing weekend and we got so much more! Our stay at Great Oak was a true retreat and a trip through time. The grandeur and stoic beauty of the estate is the perfect complement to the magnificence of its natural surroundings. The panoramic view of the water is hypnotic. The glittering history of Great Oak in its heyday gives you access to old world glamour. We truly felt transported and luxuriated in our room, which was both elegant and cozy. Our hosts, John and Cassandra, made us feel truly at home and ensured that we were taken care of yet also given the space to enjoy our down time. We are already planning a return trip!

  • Stayed February 2012, traveled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank Mary0810
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Level Contributor
19 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 12 helpful votes
5 of 5 bubbles Reviewed February 2, 2012

The Great Oak Manor is nestled in the woods with views of the Chester River. A warm welcome by the innkeeper Cassandra and her staff assured us of a great evening. The room was spacious, warm, and inviting. Cassandra took us on a tour of this grand establishment; a former hunting lodge. You could get lost in the spaciousness. Cassandra also took care of our dinner reservations without hesitation. We enjoyed a lovely evening at the Imperial Hotel in Chestertown. The food was perfect and the atmosphere quiet and cozy; just what we were looking for after a long day.
We were extremely comfortable at the inn and the amenities allowed us time to relax and enjoy the evening. Sherry or port is waiting for you in the living room; allowing you to relax and enjoy the evening even further. In the morning, coffee was waiting in the parlor and when we went down to the dining room we were met by John and Cassandra. A full breakfast is served; warm cranberry muffins, fruit, juice, coffee, and a hot dish. We were so full that we didn't stop on our journey home for lunch. All in all, our stay was wonderful. The room was very clean, the service fantastic; it had all the comforts of our own home. We will visit again!

  • Stayed January 2012, traveled with family
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank slojoed
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Annapolis, Maryland
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed November 16, 2011

My wife and I can't say enough great things about the innkeepers Cassandra and John, and their staff. We would run out of superlatives. They all contributed to making my birthday celebration a memorable one. If you get a chance, visit them once, and you will be hooked for life.

Room Tip: Ask for the corner suite in the back of the manor.
See more room tips
  • Stayed November 2011, traveled with friends
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank Chip T
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Washington DC, District of Columbia
1 review
5 of 5 bubbles Reviewed November 14, 2011

I recently went to the Great Oak Manor for a "Mommy's weekend off" sponsored by my husband. We had been there together numerous times, but this time it was just me. I loved it, of course! My room was perfect... saw the eagle in the yard! Cassandra was warm and welcoming and confirmed for me, once again, that she runs an excellent inn. The weekend was exactly what I hoped for and I have her to thank. She made me feel like her home was mine, too.

  • Stayed October 2011, traveled solo
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank Beth W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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Additional Information about Great Oak Manor

Property: Great Oak Manor
Address: 10568 Cliff Rd, Chestertown, MD 21620
Phone Number:
Location: United States > Maryland > Chestertown
Amenities:
Bar / Lounge Beach Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Pets Allowed ( Dog / Pet Friendly ) Suites
Hotel Style:
Ranked #2 of 11 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $$
Hotel Class:3.5 star — Great Oak Manor 3.5*
Number of rooms: 12
Official Description (provided by the hotel):
Great Oak Manor is located on Maryland's Eastern Shore, where the Chesapeake Bay is aglow in vibrant, warm sunsets; where towering oaks gently kiss the skyline; and where you can let your body rest and your mind wander. Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century country-style estate rests alongside the Chesapeake Bay waterfront. With 12 guestrooms and various common rooms, Great Oak Manor offers the finest in a romantic luxury bed and breakfast inn, where all of your whims are cared for, day and night. Whether you're adventurous, need to get away, or just want to be taken care of, there's something here for everyone. Spend an afternoon perusing the quaint streets of historic Chestertown, exploring the Eastern Neck Refuge, sampling the fresh catch in Rock Hall, or just curl up in the arms of a weathered Adirondack chair to soak up the view. Aside from offering a relaxing getaway for travelers, Great Oak Manor also serves as the ideal location for various events, retreats, parties, and weddings. Welcome to our home, stay a while. ... more   less 
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Also Known As:
Great Oak Manor Hotel Chestertown

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