Great Oak Manor

Chestertown, Maryland

8.3
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About the Hotel

Step off the fast track to a place and time where the elegant living of yesteryear has been beautifully preserved. At Great Oak Manor in Chestertown, Maryland, the closest highway is the duck flyway and the only traffic you'll see from your charming Georgian-style guestroom are boats sailing on crystal waters. Within this magnificent country estate, recognized by American Historic Inns as among the Top Ten Most Romantic Inns, you'll luxuriate in that "get away from it all" feeling in a private and secluded locale on Chesapeake Bay.

Location

Great Oak Manor
10568 Cliff Rd.
Chestertown, Maryland 21620

Nearest Airport: MTN

Features and Amenities

  • Dining
  • Dining Room
  • In-Room Amenities
  • WiFi

Reviews for Great Oak Manor

THE ELEGANT GREAT OAK MANOR EXPERIENCE

TripAdvisor Traveler Review Rating Reviewed 4 days ago

My recent stay at Great Oak Manor was outstanding in every way. The property is beautiful and the Manor itself is elegant. My room was spacious and beautifully appointed. The bed was the first thing I noticed when entering the room, the comforter and pillows were luxurious and artfully arranged and it was very comfortable. The room contained a seating area and table in front of a fireplace; a chair and a desk in a corner as well as a TV and side tables. There was a large closet with hangers and shelves and a beautiful bathroom, which included items not usually provided by most hotels now - shower cap, mouth wash, sewing kit, etc. I received a call from the staff several days prior to arrival with questions about any food allergies and preferences. The food reflected my stated preferences and was delicious. The chef came into the dining room to greet us and and to ensure that we were enjoying the food. The staff was wonderful - very attentive, friendly, professional. Everything was prepared in anticipation of our needs and wants and we were told to ask for anything that we might need or want. It was just a wonderful experience, we were treated as if we were guests in their home. I have been telling friends and family how much I enjoyed the Great Oak Manor Experience and I highly recommend it.

Veronica H - Charleston, South Carolina


An Enchanting Getaway

TripAdvisor Traveler Review Rating Reviewed 4 days ago

I thoroughly enjoyed my stay at Great Oak Manor. From arrival to departure, I was treated with great care and attentiveness. I was amazed by the beautiful decor and attention to detail. The rooms were beautifully appointed and clean. The grounds were immaculate and the aura surrounding the manor was serene and just perfect for rest and reflection. The meals were meticulously prepared and were delectable! The wine machine and the private beach were the icing on the cake! I could not recommend this retreat more highly!!

owensdoretha


Idyllic

TripAdvisor Traveler Review Rating Reviewed 1 week ago

The 5-star rating, the great reviews, the amazing service and the feel you get just from the photos online are all validated from the moment you arrive to the end of your stay at the Great Oak Manor. The Manor house, the rooms, the setting right on the Chesapeake Bay, the attentiveness of the staff are simply the best you can hope for. My wife and I celebrated our 60th anniversary with a 3-night stay and it was like a 2nd honeymoon. This is an idyllic getaway where the hectic pace of life across the bay just seemed to melt away. It's not inexpensive but worth it.

Hal K


Awesome place to celebrate a special occasion

TripAdvisor Traveler Review Rating Reviewed 2 weeks ago

The renovations are fantastic. The staff is amazing. The new lounge area is cozy and inviting. The dinning experience was fabulous. They made our anniversary celebration super special. We couldn’t have been happier.

Lucile L


Accommodations and service are top tier at Great Oak

TripAdvisor Traveler Review Rating Reviewed 2 weeks ago

We spent two days at the inn and enjoyed thoroughly every aspect; reception, staff, amenities, outdoor and indoor sitting areas, and the delicious breakfast! It’s clear the owners care deeply about their guests. Thank you for a splendid weekend!

EricT330 - Drexel Hill, Pennsylvania


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