Great Oak Manor
Chestertown, Maryland
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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
A little slice of heaven….
This Inn is the perfect hideaway for couples, a solo traveler and group retreats. From the moment I pulled up to the Great Oak Manor the smiles, the service, the food, the beautiful grounds, all exceeded m expectations. Each room beautifully decorated and distinct ( some with fireplaces). It was a time to refresh, renew, reset, regenerate and relax. You will see me again
MissOPJ
Place of Peace, Beauty and Tranquility
This is such a great location to disconnect from the world to re-focus and re-center yourself. The grounds are beautiful, the staff is absolutely pleasant and I had a wonderful weekend experience here! It’s a great venue for retreats and a romantic venue for couples. Highly recommended!
Roy L - Union, United States
Outstanding Choice on the Eastern Shore
Great Oak Manor is such a magnificent getaway on the Eastern Shore. The family who owns and operates the property offer the highest level of hospitality that instantly makes you feel like a friend. They organized a trip to three local farms to see the incredible local produce and dairy products available in the region, much of with they cook with at the restaurant. Quiet, luxurious accommodations right on the bay. You won't want to leave. Keep an eye out for their cool culinary experiences coming in 2025.
laurahN6896TJ
Glad we found out about it
Great Retreat! So glad we found out about it! Perfect weekend getaway for my wife and I to celebrate her birthday. Totally exceeded expectations. Driving in with the huge oak trees and Sweetgums to the pebble driveway....Very stately. The staff was incredibly nice/helpful and great to chat with. We had breakfast both mornings which were great and dinner one night. Dinner was fabulous! next evening we went into Chestertown and also had a great dinner. I would highly recommend. although the weather wasn't great, we still spent a fair amount of time relaxing and gazing over the Bay. The beach area is very nice and secluded. looking forward to going back. Also, very reasonably priced.
JollyScottFarm - Harrisburg, Pennsylvania
Awesome Birthday Weekend Getaway
The Great Oak Manor B&B was an amazing place to go to relax, recharge our batteries, and enjoy their outstanding cuisine! It was a fabulous way to celebrate my husband’s birthday weekend. The very attentive staff saw to our every need👍🏻👍🏻. Karen and Paul McFarlane
Karen M
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