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

Perfect Relaxing Getaway

TripAdvisor Traveler Review Rating Reviewed 2 weeks ago

I searched East Coast weekend getaways and hit a home run. From the minute we pulled up to the front door until we left we experienced the warmest hospitality, delicious food and very comfortable accommodations. The inn, the grounds and the water view are absolutely beautiful! The bald eagle sighting was a treat also. Our room was spotlessly clean and had a fireplace ( the Molton Brown toiletries were a plus too). The town is about 15 minutes away - very cute, safe, clean, walkable, unique shops and a farmer's market on Saturdays. Had a great lunch at Watershed. Special thanks to Werten, Sophia, Cameron, Corinne, Jordan, Dinora and Christy for making our weekend relaxing and enjoyable.

Kara B - Coopersburg, Pennsylvania


Excellent, welcoming

TripAdvisor Traveler Review Rating Reviewed 3 weeks ago

My stay at Great Oaks Manor was excellent. It is an intimate gem with impeccable, personalized service and thoughtful design details. And, the food is excellent!

stmccalla - Avondale Estates, Georgia


A Serene Retreat

TripAdvisor Traveler Review Rating Reviewed 3 weeks ago

I have participated in an annual women’s retreat here for the past four years. The moment I walk into the door, I feel at peace and serenity takes over. From the staff who pay such attention to detail and treat you warmly and hospitably, to the welcoming beautiful library, the well-appointed bar, the delicious food, and the comfy beds, the whole experience is simply exquisite. It’s hard to beat such personalized service this day and age. I keep returning year after year, and every year they exceed my expectations!

mwimes - Kansas City, Missouri


10/10 Would Highly Recommend

TripAdvisor Traveler Review Rating Reviewed 1 month ago

Great Oak Manor is an absolute gem and place I would highly recommend. From the moment you arrive, you’re surrounded by breathtaking views, warm hospitality, and a peaceful atmosphere that instantly helps you relax. The service is truly exceptional. The staff goes above and beyond to make guests feel special, offering genuine kindness and attentiveness that you rarely find. The food was delicious, breakfast, lunch, and dinner. Great Oak Manor delivers an unforgettable experience. Once you visit, you’ll already be planning your return!

Paulette B


A happy writers retreat

TripAdvisor Traveler Review Rating Reviewed 1 month ago

I spent 4 wonderful days at the Manor, on a writers conference. The incredibly kind staff, the accommodations were 5 star, the food was so thoughtfully made and fantastic and the entire atmosphere was so perfect for our group. This place was a total gem, as were the owners. Can’t wait to go back!

Lindsey P - Anaheim, California


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